[ CAS No. 1088965-37-0 ] {[proInfo.proName]}

Name: 1088965-37-0|3-Chloro-N-((S)-1-(2-(dimethylamino)acetamido)-3-(4-(8-((S)-1-hydroxyethyl)imidazo[1,2-a]pyridin-2-yl)phenyl)propan-2-yl)-4-isopropoxybenzamide|98%
Brand: Ambeed
SKU: A231503
Price: 17.0 USD
Availability: InStock
Rating: 97 (35 reviews)

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2D 3D

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Quality Control of [ 1088965-37-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1088965-37-0 ]

SDS Specification

Alternatived Products of [ 1088965-37-0 ]

Product Details of [ 1088965-37-0 ]

CAS No. :	1088965-37-0	MDL No. :	MFCD16038931
Formula :	C₃₂H₃₈ClN₅O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WHMXDBPHBVLYRC-OFVILXPXSA-N
M.W :	592.13	Pubchem ID :	46898058
Synonyms :	GSK923295A

Calculated chemistry of [ 1088965-37-0 ]

Physicochemical Properties

Num. heavy atoms :	42
Num. arom. heavy atoms :	21
Fraction Csp3 :	0.34
Num. rotatable bonds :	14
Num. H-bond acceptors :	6.0
Num. H-bond donors :	3.0
Molar Refractivity :	164.9
TPSA :	108.2 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-6.35 cm/s

Lipophilicity

Log Po/w (iLOGP) :	4.87
Log Po/w (XLOGP3) :	5.02
Log Po/w (WLOGP) :	4.19
Log Po/w (MLOGP) :	2.13
Log Po/w (SILICOS-IT) :	4.79
Consensus Log Po/w :	4.2

Druglikeness

Lipinski :	1.0
Ghose :	None
Veber :	1.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-6.12
Solubility :	0.000449 mg/ml ; 0.000000759 mol/l
Class :	Poorly soluble
Log S (Ali) :	-7.03
Solubility :	0.0000549 mg/ml ; 0.0000000928 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-9.24
Solubility :	0.000000338 mg/ml ; 0.0000000006 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	3.0
Synthetic accessibility :	4.84

Safety of [ 1088965-37-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1088965-37-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 1088965-37-0 ]
Downstream synthetic route of [ 1088965-37-0 ]

[ 1088965-37-0 ] Synthesis Path-Upstream 1~24

1
[ 1118-68-9 ]
[ 1240137-87-4 ]
[ 1088965-37-0 ]

Reference： [1] Organic Process Research and Development, 2010, vol. 14, # 5, p. 1254 - 1263

2
[ 120-47-8 ]
[ 1088965-37-0 ]

Reference： [1] Organic Process Research and Development, 2010, vol. 14, # 5, p. 1254 - 1263
[2] Organic Process Research and Development, 2010, vol. 14, # 5, p. 1254 - 1263
[3] Organic Process Research and Development, 2010, vol. 14, # 5, p. 1254 - 1263
[4] Organic Process Research and Development, 2010, vol. 14, # 5, p. 1254 - 1263
[5] Organic Process Research and Development, 2010, vol. 14, # 5, p. 1254 - 1263
[6] Organic Process Research and Development, 2010, vol. 14, # 5, p. 1254 - 1263

3
[ 3182-95-4 ]
[ 1088965-37-0 ]

4
[ 13205-46-4 ]
[ 1088965-37-0 ]

5
[ 122488-52-2 ]
[ 1088965-37-0 ]

6
[ 213598-07-3 ]
[ 1088965-37-0 ]

7
[ 66605-57-0 ]
[ 1088965-37-0 ]

8
[ 213767-19-2 ]
[ 1088965-37-0 ]

9
[ 854760-84-2 ]
[ 1088965-37-0 ]

10
[ 1208246-04-1 ]
[ 1088965-37-0 ]

11
[ 869567-97-5 ]
[ 1088965-37-0 ]

12
[ 936718-00-2 ]
[ 1088965-37-0 ]

13
[ 1240137-64-7 ]
[ 1088965-37-0 ]

14
[ 1240137-91-0 ]
[ 1088965-37-0 ]

15
[ 1240137-67-0 ]
[ 1088965-37-0 ]

16
[ 1240137-75-0 ]
[ 1088965-37-0 ]

17
[ 1240137-81-8 ]
[ 1088965-37-0 ]

18
[ 869567-96-4 ]
[ 1088965-37-0 ]

19
[ 126301-19-7 ]
[ 1088965-37-0 ]

20
[ 187526-92-7 ]
[ 1088965-37-0 ]

21
[ 62129-39-9 ]
[ 1088965-37-0 ]

22
[ 1240137-87-4 ]
[ 1088965-37-0 ]

Reference： [1] Organic Process Research and Development, 2010, vol. 14, # 5, p. 1254 - 1263

23
[ 1240137-87-4 ]
[ 1088965-37-0 ]

Reference： [1] Organic Process Research and Development, 2010, vol. 14, # 5, p. 1254 - 1263

24
[ 124-40-3 ]
[ 1088965-37-0 ]

Reference： [1] Organic Process Research and Development, 2010, vol. 14, # 5, p. 1254 - 1263

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Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1.1: potassium hydroxide / dimethyl sulfoxide / 1 h / 50 °C 1.2: 50 °C 2.1: water; potassium hydroxide / dimethyl sulfoxide / 80 - 85 °C 2.2: 50 - 60 °C 3.1: N-chloro-succinimide / N,N-dimethyl-formamide / 18 h / 22 °C 4.1: oxalyl dichloride; N,N-dimethyl-formamide / toluene / 1 h / 45 °C 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / Large scale reaction 5.2: 0 °C / Large scale reaction 6.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 6.2: 40 °C 7.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 20 °C
	Multi-step reaction with 7 steps 1.1: potassium hydroxide / dimethyl sulfoxide / 1 h / 50 °C 1.2: 50 °C 2.1: water; potassium hydroxide / dimethyl sulfoxide / 80 - 85 °C 2.2: 50 - 60 °C 3.1: N-chloro-succinimide / N,N-dimethyl-formamide / 18 h / 22 °C 4.1: oxalyl dichloride; N,N-dimethyl-formamide / toluene / 1 h / 45 °C 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / Large scale reaction 5.2: 0 °C / Large scale reaction 6.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 6.2: 40 °C 7.1: 2-methyltetrahydrofuran / 22 °C
	Multi-step reaction with 8 steps 1.1: potassium hydroxide / dimethyl sulfoxide / 1 h / 50 °C 1.2: 50 °C 2.1: water; potassium hydroxide / dimethyl sulfoxide / 80 - 85 °C 2.2: 50 - 60 °C 3.1: N-chloro-succinimide / N,N-dimethyl-formamide / 18 h / 22 °C 4.1: oxalyl dichloride; N,N-dimethyl-formamide / toluene / 1 h / 45 °C 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / Large scale reaction 5.2: 0 °C / Large scale reaction 6.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 6.2: 40 °C 7.1: dipotassium hydrogenphosphate / 2-methyltetrahydrofuran; water / 10 °C 8.1: 2-methyltetrahydrofuran; water / 4 h / 40 °C

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0 - 20 °C / Large scale reaction 2.1: bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 5 h / Reflux; Large scale reaction 3.1: N-Bromosuccinimide / tetrahydrofuran; water / 0 - 10 °C / Large scale reaction 4.1: sodium hydrogencarbonate / acetonitrile / 3 h / Reflux; Large scale reaction 5.1: hydrogenchloride / 1,4-dioxane / 2 h / 25 °C / Large scale reaction 6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / Large scale reaction 6.2: 0 °C / Large scale reaction 7.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 7.2: 40 °C 8.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 20 °C
	Multi-step reaction with 8 steps 1.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0 - 20 °C / Large scale reaction 2.1: bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 5 h / Reflux; Large scale reaction 3.1: N-Bromosuccinimide / tetrahydrofuran; water / 0 - 10 °C / Large scale reaction 4.1: sodium hydrogencarbonate / acetonitrile / 3 h / Reflux; Large scale reaction 5.1: hydrogenchloride / 1,4-dioxane / 2 h / 25 °C / Large scale reaction 6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / Large scale reaction 6.2: 0 °C / Large scale reaction 7.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 7.2: 40 °C 8.1: 2-methyltetrahydrofuran / 22 °C
	Multi-step reaction with 9 steps 1.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0 - 20 °C / Large scale reaction 2.1: bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 5 h / Reflux; Large scale reaction 3.1: N-Bromosuccinimide / tetrahydrofuran; water / 0 - 10 °C / Large scale reaction 4.1: sodium hydrogencarbonate / acetonitrile / 3 h / Reflux; Large scale reaction 5.1: hydrogenchloride / 1,4-dioxane / 2 h / 25 °C / Large scale reaction 6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / Large scale reaction 6.2: 0 °C / Large scale reaction 7.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 7.2: 40 °C 8.1: dipotassium hydrogenphosphate / 2-methyltetrahydrofuran; water / 10 °C 9.1: 2-methyltetrahydrofuran; water / 4 h / 40 °C

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: N-Bromosuccinimide / tetrahydrofuran; water / 0 - 10 °C / Large scale reaction 2.1: sodium hydrogencarbonate / acetonitrile / 3 h / Reflux; Large scale reaction 3.1: hydrogenchloride / 1,4-dioxane / 2 h / 25 °C / Large scale reaction 4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / Large scale reaction 4.2: 0 °C / Large scale reaction 5.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 5.2: 40 °C 6.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 20 °C
	Multi-step reaction with 6 steps 1.1: N-Bromosuccinimide / tetrahydrofuran; water / 0 - 10 °C / Large scale reaction 2.1: sodium hydrogencarbonate / acetonitrile / 3 h / Reflux; Large scale reaction 3.1: hydrogenchloride / 1,4-dioxane / 2 h / 25 °C / Large scale reaction 4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / Large scale reaction 4.2: 0 °C / Large scale reaction 5.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 5.2: 40 °C 6.1: 2-methyltetrahydrofuran / 22 °C
	Multi-step reaction with 7 steps 1.1: N-Bromosuccinimide / tetrahydrofuran; water / 0 - 10 °C / Large scale reaction 2.1: sodium hydrogencarbonate / acetonitrile / 3 h / Reflux; Large scale reaction 3.1: hydrogenchloride / 1,4-dioxane / 2 h / 25 °C / Large scale reaction 4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / Large scale reaction 4.2: 0 °C / Large scale reaction 5.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 5.2: 40 °C 6.1: dipotassium hydrogenphosphate / 2-methyltetrahydrofuran; water / 10 °C 7.1: 2-methyltetrahydrofuran; water / 4 h / 40 °C

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: sodium hydrogencarbonate / acetonitrile / 3 h / Reflux; Large scale reaction 2.1: hydrogenchloride / 1,4-dioxane / 2 h / 25 °C / Large scale reaction 3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / Large scale reaction 3.2: 0 °C / Large scale reaction 4.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 4.2: 40 °C 5.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 20 °C
	Multi-step reaction with 5 steps 1.1: sodium hydrogencarbonate / acetonitrile / 3 h / Reflux; Large scale reaction 2.1: hydrogenchloride / 1,4-dioxane / 2 h / 25 °C / Large scale reaction 3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / Large scale reaction 3.2: 0 °C / Large scale reaction 4.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 4.2: 40 °C 5.1: 2-methyltetrahydrofuran / 22 °C
	Multi-step reaction with 6 steps 1.1: sodium hydrogencarbonate / acetonitrile / 3 h / Reflux; Large scale reaction 2.1: hydrogenchloride / 1,4-dioxane / 2 h / 25 °C / Large scale reaction 3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / Large scale reaction 3.2: 0 °C / Large scale reaction 4.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 4.2: 40 °C 5.1: dipotassium hydrogenphosphate / 2-methyltetrahydrofuran; water / 10 °C 6.1: 2-methyltetrahydrofuran; water / 4 h / 40 °C

[ CAS No. 1088965-37-0 ] {[proInfo.proName]}

Quality Control of [ 1088965-37-0 ]

Related Doc. of [ 1088965-37-0 ]

Product Details of [ 1088965-37-0 ]

Calculated chemistry of [ 1088965-37-0 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1088965-37-0 ]

Application In Synthesis of [ 1088965-37-0 ]

[ 1088965-37-0 ] Synthesis Path-Upstream 1~24

[ 1088965-37-0 ] Synthesis Path-Downstream 1~25

Precautionary Statements-General

Prevention

Response

Storage

Disposal

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Inquiry

	Multi-step reaction with 8 steps 1.1: potassium hydroxide / dimethyl sulfoxide / 1 h / 50 °C 1.2: 50 °C 2.1: water; potassium hydroxide / dimethyl sulfoxide / 80 - 85 °C 2.2: 50 - 60 °C 3.1: N-chloro-succinimide / N,N-dimethyl-formamide / 18 h / 22 °C 4.1: oxalyl dichloride; N,N-dimethyl-formamide / toluene / 1 h / 45 °C 5.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 5 - 8 °C 6.1: tetrabutylammomium bromide; sodium hydrogencarbonate / acetonitrile / 26 h / Reflux; Large scale reaction 7.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 7.2: 40 °C 8.1: 2-methyltetrahydrofuran / 22 °C
	Multi-step reaction with 8 steps 1.1: potassium hydroxide / dimethyl sulfoxide / 1 h / 50 °C 1.2: 50 °C 2.1: water; potassium hydroxide / dimethyl sulfoxide / 80 - 85 °C 2.2: 50 - 60 °C 3.1: N-chloro-succinimide / N,N-dimethyl-formamide / 18 h / 22 °C 4.1: oxalyl dichloride; N,N-dimethyl-formamide / toluene / 1 h / 45 °C 5.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 5 - 8 °C 6.1: tetrabutylammomium bromide; sodium hydrogencarbonate / acetonitrile / 26 h / Reflux; Large scale reaction 7.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 7.2: 40 °C 8.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 20 °C
	Multi-step reaction with 9 steps 1.1: potassium hydroxide / dimethyl sulfoxide / 1 h / 50 °C 1.2: 50 °C 2.1: water; potassium hydroxide / dimethyl sulfoxide / 80 - 85 °C 2.2: 50 - 60 °C 3.1: N-chloro-succinimide / N,N-dimethyl-formamide / 18 h / 22 °C 4.1: oxalyl dichloride; N,N-dimethyl-formamide / toluene / 1 h / 45 °C 5.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 5 - 8 °C 6.1: tetrabutylammomium bromide; sodium hydrogencarbonate / acetonitrile / 26 h / Reflux; Large scale reaction 7.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 7.2: 40 °C 8.1: dipotassium hydrogenphosphate / 2-methyltetrahydrofuran; water / 10 °C 9.1: 2-methyltetrahydrofuran; water / 4 h / 40 °C

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: tetrabutylammomium bromide; sodium hydrogencarbonate / acetonitrile / 26 h / Reflux; Large scale reaction 2.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 2.2: 40 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 20 °C
	Multi-step reaction with 3 steps 1.1: tetrabutylammomium bromide; sodium hydrogencarbonate / acetonitrile / 26 h / Reflux; Large scale reaction 2.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 2.2: 40 °C 3.1: 2-methyltetrahydrofuran / 22 °C
	Multi-step reaction with 4 steps 1.1: tetrabutylammomium bromide; sodium hydrogencarbonate / acetonitrile / 26 h / Reflux; Large scale reaction 2.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 2.2: 40 °C 3.1: dipotassium hydrogenphosphate / 2-methyltetrahydrofuran; water / 10 °C 4.1: 2-methyltetrahydrofuran; water / 4 h / 40 °C

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: hydrogenchloride / 1,4-dioxane / 2 h / 25 °C / Large scale reaction 2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / Large scale reaction 2.2: 0 °C / Large scale reaction 3.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 3.2: 40 °C 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 20 °C
	Multi-step reaction with 4 steps 1.1: hydrogenchloride / 1,4-dioxane / 2 h / 25 °C / Large scale reaction 2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / Large scale reaction 2.2: 0 °C / Large scale reaction 3.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 3.2: 40 °C 4.1: 2-methyltetrahydrofuran / 22 °C
	Multi-step reaction with 5 steps 1.1: hydrogenchloride / 1,4-dioxane / 2 h / 25 °C / Large scale reaction 2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / Large scale reaction 2.2: 0 °C / Large scale reaction 3.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 3.2: 40 °C 4.1: dipotassium hydrogenphosphate / 2-methyltetrahydrofuran; water / 10 °C 5.1: 2-methyltetrahydrofuran; water / 4 h / 40 °C

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / Large scale reaction 1.2: 0 °C / Large scale reaction 2.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 2.2: 40 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 20 °C
	Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / Large scale reaction 1.2: 0 °C / Large scale reaction 2.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 2.2: 40 °C 3.1: 2-methyltetrahydrofuran / 22 °C
	Multi-step reaction with 4 steps 1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / Large scale reaction 1.2: 0 °C / Large scale reaction 2.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 2.2: 40 °C 3.1: dipotassium hydrogenphosphate / 2-methyltetrahydrofuran; water / 10 °C 4.1: 2-methyltetrahydrofuran; water / 4 h / 40 °C

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 1.2: 40 °C 2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 20 °C
	Multi-step reaction with 2 steps 1.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 1.2: 40 °C 2.1: 2-methyltetrahydrofuran / 22 °C
	Multi-step reaction with 3 steps 1.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 1.2: 40 °C 2.1: dipotassium hydrogenphosphate / 2-methyltetrahydrofuran; water / 10 °C 3.1: 2-methyltetrahydrofuran; water / 4 h / 40 °C

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 5 - 8 °C 2.1: tetrabutylammomium bromide; sodium hydrogencarbonate / acetonitrile / 26 h / Reflux; Large scale reaction 3.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 3.2: 40 °C 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 20 °C
	Multi-step reaction with 4 steps 1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 5 - 8 °C 2.1: tetrabutylammomium bromide; sodium hydrogencarbonate / acetonitrile / 26 h / Reflux; Large scale reaction 3.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 3.2: 40 °C 4.1: 2-methyltetrahydrofuran / 22 °C
	Multi-step reaction with 5 steps 1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 5 - 8 °C 2.1: tetrabutylammomium bromide; sodium hydrogencarbonate / acetonitrile / 26 h / Reflux; Large scale reaction 3.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 3.2: 40 °C 4.1: dipotassium hydrogenphosphate / 2-methyltetrahydrofuran; water / 10 °C 5.1: 2-methyltetrahydrofuran; water / 4 h / 40 °C

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1.1: bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 5 h / Reflux; Large scale reaction 2.1: N-Bromosuccinimide / tetrahydrofuran; water / 0 - 10 °C / Large scale reaction 3.1: sodium hydrogencarbonate / acetonitrile / 3 h / Reflux; Large scale reaction 4.1: hydrogenchloride / 1,4-dioxane / 2 h / 25 °C / Large scale reaction 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / Large scale reaction 5.2: 0 °C / Large scale reaction 6.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 6.2: 40 °C 7.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 20 °C
	Multi-step reaction with 7 steps 1.1: bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 5 h / Reflux; Large scale reaction 2.1: N-Bromosuccinimide / tetrahydrofuran; water / 0 - 10 °C / Large scale reaction 3.1: sodium hydrogencarbonate / acetonitrile / 3 h / Reflux; Large scale reaction 4.1: hydrogenchloride / 1,4-dioxane / 2 h / 25 °C / Large scale reaction 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / Large scale reaction 5.2: 0 °C / Large scale reaction 6.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 6.2: 40 °C 7.1: 2-methyltetrahydrofuran / 22 °C
	Multi-step reaction with 8 steps 1.1: bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 5 h / Reflux; Large scale reaction 2.1: N-Bromosuccinimide / tetrahydrofuran; water / 0 - 10 °C / Large scale reaction 3.1: sodium hydrogencarbonate / acetonitrile / 3 h / Reflux; Large scale reaction 4.1: hydrogenchloride / 1,4-dioxane / 2 h / 25 °C / Large scale reaction 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / Large scale reaction 5.2: 0 °C / Large scale reaction 6.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 6.2: 40 °C 7.1: dipotassium hydrogenphosphate / 2-methyltetrahydrofuran; water / 10 °C 8.1: 2-methyltetrahydrofuran; water / 4 h / 40 °C

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1.1: ethyl acetate / 1.5 h 2.1: di-isopropyl azodicarboxylate; triphenylphosphine / methanol; toluene / 42 - 60 °C 2.2: 2 h / 60 °C 3.1: aluminum (III) chloride / 22 h / -5 °C 3.2: 35 - 50 °C 3.3: 18 h / 65 °C 4.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 5 - 8 °C 5.1: tetrabutylammomium bromide; sodium hydrogencarbonate / acetonitrile / 26 h / Reflux; Large scale reaction 6.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 6.2: 40 °C 7.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 20 °C
	Multi-step reaction with 10 steps 1.1: ethyl acetate / 1.5 h 2.1: triethylamine / ethyl acetate / 0 - 4 °C / Large scale reaction 3.1: tetrabutylammomium bromide / Isopropyl acetate / 23 h / 35 °C / Large scale reaction 4.1: hydrogenchloride; water / methanol / 3.25 h / 60 °C 5.1: aluminum (III) chloride / 22 h / -5 °C 5.2: 35 - 50 °C 5.3: 18 h / 65 °C 6.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 5 - 8 °C 7.1: tetrabutylammomium bromide; sodium hydrogencarbonate / acetonitrile / 26 h / Reflux; Large scale reaction 8.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 8.2: 40 °C 9.1: dipotassium hydrogenphosphate / 2-methyltetrahydrofuran; water / 10 °C 10.1: 2-methyltetrahydrofuran; water / 4 h / 40 °C
	Multi-step reaction with 7 steps 1.1: ethyl acetate / 1.5 h 2.1: di-isopropyl azodicarboxylate; triphenylphosphine / methanol; toluene / 42 - 60 °C 2.2: 2 h / 60 °C 3.1: aluminum (III) chloride / 22 h / -5 °C 3.2: 35 - 50 °C 3.3: 18 h / 65 °C 4.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 5 - 8 °C 5.1: tetrabutylammomium bromide; sodium hydrogencarbonate / acetonitrile / 26 h / Reflux; Large scale reaction 6.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 6.2: 40 °C 7.1: 2-methyltetrahydrofuran / 22 °C

	Multi-step reaction with 8 steps 1.1: ethyl acetate / 1.5 h 2.1: di-isopropyl azodicarboxylate; triphenylphosphine / methanol; toluene / 42 - 60 °C 2.2: 2 h / 60 °C 3.1: aluminum (III) chloride / 22 h / -5 °C 3.2: 35 - 50 °C 3.3: 18 h / 65 °C 4.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 5 - 8 °C 5.1: tetrabutylammomium bromide; sodium hydrogencarbonate / acetonitrile / 26 h / Reflux; Large scale reaction 6.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 6.2: 40 °C 7.1: dipotassium hydrogenphosphate / 2-methyltetrahydrofuran; water / 10 °C 8.1: 2-methyltetrahydrofuran; water / 4 h / 40 °C
	Multi-step reaction with 9 steps 1.1: ethyl acetate / 1.5 h 2.1: triethylamine / ethyl acetate / 0 - 4 °C / Large scale reaction 3.1: tetrabutylammomium bromide / Isopropyl acetate / 23 h / 35 °C / Large scale reaction 4.1: hydrogenchloride; water / methanol / 3.25 h / 60 °C 5.1: aluminum (III) chloride / 22 h / -5 °C 5.2: 35 - 50 °C 5.3: 18 h / 65 °C 6.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 5 - 8 °C 7.1: tetrabutylammomium bromide; sodium hydrogencarbonate / acetonitrile / 26 h / Reflux; Large scale reaction 8.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 8.2: 40 °C 9.1: 2-methyltetrahydrofuran / 22 °C
	Multi-step reaction with 9 steps 1.1: ethyl acetate / 1.5 h 2.1: triethylamine / ethyl acetate / 0 - 4 °C / Large scale reaction 3.1: tetrabutylammomium bromide / Isopropyl acetate / 23 h / 35 °C / Large scale reaction 4.1: hydrogenchloride; water / methanol / 3.25 h / 60 °C 5.1: aluminum (III) chloride / 22 h / -5 °C 5.2: 35 - 50 °C 5.3: 18 h / 65 °C 6.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 5 - 8 °C 7.1: tetrabutylammomium bromide; sodium hydrogencarbonate / acetonitrile / 26 h / Reflux; Large scale reaction 8.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 8.2: 40 °C 9.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 20 °C

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: water; potassium hydroxide / dimethyl sulfoxide / 80 - 85 °C 1.2: 50 - 60 °C 2.1: N-chloro-succinimide / N,N-dimethyl-formamide / 18 h / 22 °C 3.1: oxalyl dichloride; N,N-dimethyl-formamide / toluene / 1 h / 45 °C 4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / Large scale reaction 4.2: 0 °C / Large scale reaction 5.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 5.2: 40 °C 6.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 20 °C
	Multi-step reaction with 6 steps 1.1: water; potassium hydroxide / dimethyl sulfoxide / 80 - 85 °C 1.2: 50 - 60 °C 2.1: N-chloro-succinimide / N,N-dimethyl-formamide / 18 h / 22 °C 3.1: oxalyl dichloride; N,N-dimethyl-formamide / toluene / 1 h / 45 °C 4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / Large scale reaction 4.2: 0 °C / Large scale reaction 5.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 5.2: 40 °C 6.1: 2-methyltetrahydrofuran / 22 °C
	Multi-step reaction with 7 steps 1.1: water; potassium hydroxide / dimethyl sulfoxide / 80 - 85 °C 1.2: 50 - 60 °C 2.1: N-chloro-succinimide / N,N-dimethyl-formamide / 18 h / 22 °C 3.1: oxalyl dichloride; N,N-dimethyl-formamide / toluene / 1 h / 45 °C 4.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 5 - 8 °C 5.1: tetrabutylammomium bromide; sodium hydrogencarbonate / acetonitrile / 26 h / Reflux; Large scale reaction 6.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 6.2: 40 °C 7.1: 2-methyltetrahydrofuran / 22 °C

	Multi-step reaction with 7 steps 1.1: water; potassium hydroxide / dimethyl sulfoxide / 80 - 85 °C 1.2: 50 - 60 °C 2.1: N-chloro-succinimide / N,N-dimethyl-formamide / 18 h / 22 °C 3.1: oxalyl dichloride; N,N-dimethyl-formamide / toluene / 1 h / 45 °C 4.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 5 - 8 °C 5.1: tetrabutylammomium bromide; sodium hydrogencarbonate / acetonitrile / 26 h / Reflux; Large scale reaction 6.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 6.2: 40 °C 7.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 20 °C
	Multi-step reaction with 7 steps 1.1: water; potassium hydroxide / dimethyl sulfoxide / 80 - 85 °C 1.2: 50 - 60 °C 2.1: N-chloro-succinimide / N,N-dimethyl-formamide / 18 h / 22 °C 3.1: oxalyl dichloride; N,N-dimethyl-formamide / toluene / 1 h / 45 °C 4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / Large scale reaction 4.2: 0 °C / Large scale reaction 5.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 5.2: 40 °C 6.1: dipotassium hydrogenphosphate / 2-methyltetrahydrofuran; water / 10 °C 7.1: 2-methyltetrahydrofuran; water / 4 h / 40 °C
	Multi-step reaction with 8 steps 1.1: water; potassium hydroxide / dimethyl sulfoxide / 80 - 85 °C 1.2: 50 - 60 °C 2.1: N-chloro-succinimide / N,N-dimethyl-formamide / 18 h / 22 °C 3.1: oxalyl dichloride; N,N-dimethyl-formamide / toluene / 1 h / 45 °C 4.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 5 - 8 °C 5.1: tetrabutylammomium bromide; sodium hydrogencarbonate / acetonitrile / 26 h / Reflux; Large scale reaction 6.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 6.2: 40 °C 7.1: dipotassium hydrogenphosphate / 2-methyltetrahydrofuran; water / 10 °C 8.1: 2-methyltetrahydrofuran; water / 4 h / 40 °C

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: oxalyl dichloride; N,N-dimethyl-formamide / toluene / 1 h / 45 °C 2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / Large scale reaction 2.2: 0 °C / Large scale reaction 3.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 3.2: 40 °C 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 20 °C
	Multi-step reaction with 4 steps 1.1: oxalyl dichloride; N,N-dimethyl-formamide / toluene / 1 h / 45 °C 2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / Large scale reaction 2.2: 0 °C / Large scale reaction 3.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 3.2: 40 °C 4.1: 2-methyltetrahydrofuran / 22 °C
	Multi-step reaction with 5 steps 1.1: oxalyl dichloride; N,N-dimethyl-formamide / toluene / 1 h / 45 °C 2.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 5 - 8 °C 3.1: tetrabutylammomium bromide; sodium hydrogencarbonate / acetonitrile / 26 h / Reflux; Large scale reaction 4.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 4.2: 40 °C 5.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 20 °C

	Multi-step reaction with 5 steps 1.1: oxalyl dichloride; N,N-dimethyl-formamide / toluene / 1 h / 45 °C 2.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 5 - 8 °C 3.1: tetrabutylammomium bromide; sodium hydrogencarbonate / acetonitrile / 26 h / Reflux; Large scale reaction 4.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 4.2: 40 °C 5.1: 2-methyltetrahydrofuran / 22 °C
	Multi-step reaction with 5 steps 1.1: oxalyl dichloride; N,N-dimethyl-formamide / toluene / 1 h / 45 °C 2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / Large scale reaction 2.2: 0 °C / Large scale reaction 3.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 3.2: 40 °C 4.1: dipotassium hydrogenphosphate / 2-methyltetrahydrofuran; water / 10 °C 5.1: 2-methyltetrahydrofuran; water / 4 h / 40 °C
	Multi-step reaction with 6 steps 1.1: oxalyl dichloride; N,N-dimethyl-formamide / toluene / 1 h / 45 °C 2.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 5 - 8 °C 3.1: tetrabutylammomium bromide; sodium hydrogencarbonate / acetonitrile / 26 h / Reflux; Large scale reaction 4.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 4.2: 40 °C 5.1: dipotassium hydrogenphosphate / 2-methyltetrahydrofuran; water / 10 °C 6.1: 2-methyltetrahydrofuran; water / 4 h / 40 °C

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: di-isopropyl azodicarboxylate; triphenylphosphine / methanol; toluene / 42 - 60 °C 1.2: 2 h / 60 °C 2.1: aluminum (III) chloride / 22 h / -5 °C 2.2: 35 - 50 °C 2.3: 18 h / 65 °C 3.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 5 - 8 °C 4.1: tetrabutylammomium bromide; sodium hydrogencarbonate / acetonitrile / 26 h / Reflux; Large scale reaction 5.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 5.2: 40 °C 6.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 20 °C
	Multi-step reaction with 6 steps 1.1: di-isopropyl azodicarboxylate; triphenylphosphine / methanol; toluene / 42 - 60 °C 1.2: 2 h / 60 °C 2.1: aluminum (III) chloride / 22 h / -5 °C 2.2: 35 - 50 °C 2.3: 18 h / 65 °C 3.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 5 - 8 °C 4.1: tetrabutylammomium bromide; sodium hydrogencarbonate / acetonitrile / 26 h / Reflux; Large scale reaction 5.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 5.2: 40 °C 6.1: 2-methyltetrahydrofuran / 22 °C
	Multi-step reaction with 7 steps 1.1: di-isopropyl azodicarboxylate; triphenylphosphine / methanol; toluene / 42 - 60 °C 1.2: 2 h / 60 °C 2.1: aluminum (III) chloride / 22 h / -5 °C 2.2: 35 - 50 °C 2.3: 18 h / 65 °C 3.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 5 - 8 °C 4.1: tetrabutylammomium bromide; sodium hydrogencarbonate / acetonitrile / 26 h / Reflux; Large scale reaction 5.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 5.2: 40 °C 6.1: dipotassium hydrogenphosphate / 2-methyltetrahydrofuran; water / 10 °C 7.1: 2-methyltetrahydrofuran; water / 4 h / 40 °C

	Multi-step reaction with 8 steps 1.1: triethylamine / ethyl acetate / 0 - 4 °C / Large scale reaction 2.1: tetrabutylammomium bromide / Isopropyl acetate / 23 h / 35 °C / Large scale reaction 3.1: hydrogenchloride; water / methanol / 3.25 h / 60 °C 4.1: aluminum (III) chloride / 22 h / -5 °C 4.2: 35 - 50 °C 4.3: 18 h / 65 °C 5.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 5 - 8 °C 6.1: tetrabutylammomium bromide; sodium hydrogencarbonate / acetonitrile / 26 h / Reflux; Large scale reaction 7.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 7.2: 40 °C 8.1: 2-methyltetrahydrofuran / 22 °C
	Multi-step reaction with 8 steps 1.1: triethylamine / ethyl acetate / 0 - 4 °C / Large scale reaction 2.1: tetrabutylammomium bromide / Isopropyl acetate / 23 h / 35 °C / Large scale reaction 3.1: hydrogenchloride; water / methanol / 3.25 h / 60 °C 4.1: aluminum (III) chloride / 22 h / -5 °C 4.2: 35 - 50 °C 4.3: 18 h / 65 °C 5.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 5 - 8 °C 6.1: tetrabutylammomium bromide; sodium hydrogencarbonate / acetonitrile / 26 h / Reflux; Large scale reaction 7.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 7.2: 40 °C 8.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 20 °C
	Multi-step reaction with 9 steps 1.1: triethylamine / ethyl acetate / 0 - 4 °C / Large scale reaction 2.1: tetrabutylammomium bromide / Isopropyl acetate / 23 h / 35 °C / Large scale reaction 3.1: hydrogenchloride; water / methanol / 3.25 h / 60 °C 4.1: aluminum (III) chloride / 22 h / -5 °C 4.2: 35 - 50 °C 4.3: 18 h / 65 °C 5.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 5 - 8 °C 6.1: tetrabutylammomium bromide; sodium hydrogencarbonate / acetonitrile / 26 h / Reflux; Large scale reaction 7.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 7.2: 40 °C 8.1: dipotassium hydrogenphosphate / 2-methyltetrahydrofuran; water / 10 °C 9.1: 2-methyltetrahydrofuran; water / 4 h / 40 °C

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1.1: tetrabutylammomium bromide / Isopropyl acetate / 23 h / 35 °C / Large scale reaction 2.1: hydrogenchloride; water / methanol / 3.25 h / 60 °C 3.1: aluminum (III) chloride / 22 h / -5 °C 3.2: 35 - 50 °C 3.3: 18 h / 65 °C 4.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 5 - 8 °C 5.1: tetrabutylammomium bromide; sodium hydrogencarbonate / acetonitrile / 26 h / Reflux; Large scale reaction 6.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 6.2: 40 °C 7.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 20 °C
	Multi-step reaction with 7 steps 1.1: tetrabutylammomium bromide / Isopropyl acetate / 23 h / 35 °C / Large scale reaction 2.1: hydrogenchloride; water / methanol / 3.25 h / 60 °C 3.1: aluminum (III) chloride / 22 h / -5 °C 3.2: 35 - 50 °C 3.3: 18 h / 65 °C 4.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 5 - 8 °C 5.1: tetrabutylammomium bromide; sodium hydrogencarbonate / acetonitrile / 26 h / Reflux; Large scale reaction 6.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 6.2: 40 °C 7.1: 2-methyltetrahydrofuran / 22 °C
	Multi-step reaction with 8 steps 1.1: tetrabutylammomium bromide / Isopropyl acetate / 23 h / 35 °C / Large scale reaction 2.1: hydrogenchloride; water / methanol / 3.25 h / 60 °C 3.1: aluminum (III) chloride / 22 h / -5 °C 3.2: 35 - 50 °C 3.3: 18 h / 65 °C 4.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 5 - 8 °C 5.1: tetrabutylammomium bromide; sodium hydrogencarbonate / acetonitrile / 26 h / Reflux; Large scale reaction 6.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 6.2: 40 °C 7.1: dipotassium hydrogenphosphate / 2-methyltetrahydrofuran; water / 10 °C 8.1: 2-methyltetrahydrofuran; water / 4 h / 40 °C

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: hydrogenchloride; water / methanol / 3.25 h / 60 °C 2.1: aluminum (III) chloride / 22 h / -5 °C 2.2: 35 - 50 °C 2.3: 18 h / 65 °C 3.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 5 - 8 °C 4.1: tetrabutylammomium bromide; sodium hydrogencarbonate / acetonitrile / 26 h / Reflux; Large scale reaction 5.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 5.2: 40 °C 6.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 20 °C
	Multi-step reaction with 6 steps 1.1: hydrogenchloride; water / methanol / 3.25 h / 60 °C 2.1: aluminum (III) chloride / 22 h / -5 °C 2.2: 35 - 50 °C 2.3: 18 h / 65 °C 3.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 5 - 8 °C 4.1: tetrabutylammomium bromide; sodium hydrogencarbonate / acetonitrile / 26 h / Reflux; Large scale reaction 5.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 5.2: 40 °C 6.1: 2-methyltetrahydrofuran / 22 °C
	Multi-step reaction with 7 steps 1.1: hydrogenchloride; water / methanol / 3.25 h / 60 °C 2.1: aluminum (III) chloride / 22 h / -5 °C 2.2: 35 - 50 °C 2.3: 18 h / 65 °C 3.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 5 - 8 °C 4.1: tetrabutylammomium bromide; sodium hydrogencarbonate / acetonitrile / 26 h / Reflux; Large scale reaction 5.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 5.2: 40 °C 6.1: dipotassium hydrogenphosphate / 2-methyltetrahydrofuran; water / 10 °C 7.1: 2-methyltetrahydrofuran; water / 4 h / 40 °C

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: aluminum (III) chloride / 22 h / -5 °C 1.2: 35 - 50 °C 1.3: 18 h / 65 °C 2.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 5 - 8 °C 3.1: tetrabutylammomium bromide; sodium hydrogencarbonate / acetonitrile / 26 h / Reflux; Large scale reaction 4.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 4.2: 40 °C 5.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 20 °C
	Multi-step reaction with 5 steps 1.1: aluminum (III) chloride / 22 h / -5 °C 1.2: 35 - 50 °C 1.3: 18 h / 65 °C 2.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 5 - 8 °C 3.1: tetrabutylammomium bromide; sodium hydrogencarbonate / acetonitrile / 26 h / Reflux; Large scale reaction 4.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 4.2: 40 °C 5.1: 2-methyltetrahydrofuran / 22 °C
	Multi-step reaction with 6 steps 1.1: aluminum (III) chloride / 22 h / -5 °C 1.2: 35 - 50 °C 1.3: 18 h / 65 °C 2.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 5 - 8 °C 3.1: tetrabutylammomium bromide; sodium hydrogencarbonate / acetonitrile / 26 h / Reflux; Large scale reaction 4.1: hydrazine hydrate / ethanol; tert-butyl methyl ether / 16 h / 40 °C 4.2: 40 °C 5.1: dipotassium hydrogenphosphate / 2-methyltetrahydrofuran; water / 10 °C 6.1: 2-methyltetrahydrofuran; water / 4 h / 40 °C

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling