[ CAS No. 1638761-29-1 ] {[proInfo.proName]}

Name: 1638761-29-1|tert-Butyl ((3-(hydroxymethyl)bicyclo[1.1.1]pentan-1-yl)methyl)carbamate|95%
Brand: Ambeed
SKU: A828302
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Quality Control of [ 1638761-29-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 1638761-29-1 ]

Product Details of [ 1638761-29-1 ]

CAS No. :	1638761-29-1	MDL No. :	MFCD27987012
Formula :	C₁₂H₂₁NO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WKAJJGDMKAXWMH-UHFFFAOYSA-N
M.W :	227.30	Pubchem ID :	118997546
Synonyms :

Safety of [ 1638761-29-1 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501	UN#:
Hazard Statements:	H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1638761-29-1 ]

* 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.

Downstream synthetic route of [ 1638761-29-1 ]

[ 1638761-29-1 ] Synthesis Path-Downstream 1~17

1
[ 24424-99-5 ]
[ CAS Unavailable ]
[ 1638761-29-1 ]

Yield	Reaction Conditions	Operation in experiment
75 mg	Stage #1: di-<i>tert</i>-butyl dicarbonate; C₈H₁₅NO With dimethylsulfide borane complex In tetrahydrofuran; dichloromethane for 16h; Stage #2: With potassium carbonate In tetrahydrofuran; dichloromethane for 70h;	52.D 52D. tert-butyl ((3 -(hydroxymethyl)bicyclo[ 1.1.1 Jpentan- 1 -yl)methyl)carbamate (0713) A 100 mL round-bottomed flask was charged with methyl 3 -carbarn oylbicyclo (0714) [l. l.l]pentane-l-carboxylate (133 mg, 0.786 mmol) in THF (20 mL) and methylene chloride (20 mL). Borane-dimethyl sulfide complex (5 M in ether) (0.943 mL, 4.72 mmol) was added. After stirring for 16 hours, Boc-anhydride (0.365 mL, 1.572 mmol) and potassium carbonate (435 mg, 3.14 mmol) were added. After 70 hours, the reaction was quenched with methanol. Volatiles were removed and the residue dried under high vacuum. The crude product was dissolved in a small amount of methylene chloride and charged onto a 12 g silica gel cartridge which was then eluted with 0% to 100% ethyl acetate in hexanes. Evaporation provided tert-butyl ((3- (0715) (hydroxym ethyl )bicyclo[ 1.1.1 Jpentan- l-yl)methyl)carbamate (75 mg, 42%). 'H NMR (400 MHz, CHLOROFORM-d) d 4.49 (br s, 1H), 3.63 (d, J= 5.9 Hz, 2H), 3.23 (br d, (0716) J= 5.5 Hz, 2H), 1.64 (s, 6H), 1.47 (s, 9H), 1.19 (t, =6.0 Hz, 1H).

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2020/150115, 2020, A1 Location in patent: Page/Page column 111

2
[ 56842-95-6 ]
[ 1638761-29-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: thionyl chloride / 16 h 1.2: 16 h 2.1: oxalyl dichloride / diethyl ether 3.1: ammonia / dichloromethane / 2.5 h 4.1: dimethylsulfide borane complex / dichloromethane; tetrahydrofuran / 16 h 5.1: dimethylsulfide borane complex / dichloromethane; tetrahydrofuran / 16 h 5.2: 70 h

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2020/150115, 2020, A1

3
[ 83249-10-9 ]
[ 1638761-29-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: oxalyl dichloride / diethyl ether 2.1: ammonia / dichloromethane / 2.5 h 3.1: dimethylsulfide borane complex / dichloromethane; tetrahydrofuran / 16 h 4.1: dimethylsulfide borane complex / dichloromethane; tetrahydrofuran / 16 h 4.2: 70 h

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2020/150115, 2020, A1

4
[ 110371-22-7 ]
[ 1638761-29-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: ammonia / dichloromethane / 2.5 h 2.1: dimethylsulfide borane complex / dichloromethane; tetrahydrofuran / 16 h 3.1: dimethylsulfide borane complex / dichloromethane; tetrahydrofuran / 16 h 3.2: 70 h

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2020/150115, 2020, A1

5
[ 156329-77-0 ]
[ 1638761-29-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: dimethylsulfide borane complex / dichloromethane; tetrahydrofuran / 16 h 2.1: dimethylsulfide borane complex / dichloromethane; tetrahydrofuran / 16 h 2.2: 70 h

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2020/150115, 2020, A1

6
[ 1638761-29-1 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: hydrogenchloride / 1,4-dioxane; dichloromethane / 2 h 2: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 16 h

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2020/150115, 2020, A1

7
[ 1638761-29-1 ]
[ 2458190-70-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrogenchloride In 1,4-dioxane; dichloromethane for 2h;	52.E A 50 mL round-bottomed flask was charged with tert-butyl ((3 -(hydroxymethyl) bicyclo[l.l. l]pentan-l-yl)methyl)carbamate (75 mg, 0.330 mmol) and HC1 (4N dioxane) (0.412 mL, 1.650 mmol) in methylene chloride (10 mL). The reaction was stirred for 2 hours, when the volatiles were removed and the sample dried under high vacuum to give (3-(aminomethyl)bicyclo[l. l.l]pentan-l-yl)methanol, HC1 (54 mg, 100%).

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2020/150115, 2020, A1 Location in patent: Page/Page column 112

8
[ 1638761-29-1 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: hydrogenchloride / 1,4-dioxane; dichloromethane / 2 h 2: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 16 h / 120 °C

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2020/150115, 2020, A1

9
[ 1638761-29-1 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: hydrogenchloride / 1,4-dioxane; dichloromethane / 2 h 2.1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 16 h 2.2: 3 h

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2020/150115, 2020, A1

10
[ 1638761-29-1 ]
[ 2458189-48-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: hydrogenchloride / 1,4-dioxane; dichloromethane / 2 h 2: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 16 h / 120 °C 3: trifluoroacetic acid / 1 h

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2020/150115, 2020, A1

11
[ 1638761-29-1 ]
[ 124-63-0 ]
[ 2824121-40-4 ]

Yield	Reaction Conditions	Operation in experiment
95%	With triethylamine In dichloromethane at 20℃; Cooling with ice;	General Method 1b (GM1b): chlorination via a mesylate General procedure: Methane sulfonyl chloride (2.5 eq) (0.6 mL, 8.32 mmol) was added to a solution of TEA (2.8 eq) and alcohol (1.0 eq) in DCM (20 mL) while cooling in an ice/water bath. The reaction was stirred at rt for 18 h. The reaction was diluted with DCM and washed with sat. NaHCO3 (aq). The aqueous layer was extracted with DCM (3 x 25 mL) and the combined organics were washed with brine, dried (Na2SO4), filtered and concentrated. The crude product was purified by flash chromatography.

Reference： [1]Current Patent Assignee: KALVISTA PHARMACEUTICALS INC - WO2022/175675, 2022, A1 Location in patent: Page/Page column 409; 433

12
[ 1638761-29-1 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: Dess-Martin periodane / dichloromethane / 3 h / 20 °C / Cooling with ice 1.2: 0.25 h 2.1: hydrogenchloride / 1,4-dioxane / 20 °C

Reference： [1]Current Patent Assignee: KALVISTA PHARMACEUTICALS INC - WO2022/175675, 2022, A1

13
[ 1638761-29-1 ]
[ 2824121-74-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: Dess-Martin periodane / dichloromethane / 3 h / 20 °C / Cooling with ice 1.2: 0.25 h 2.1: hydrogenchloride / 1,4-dioxane / 20 °C 3.1: Cs₂CO₃; dicyclohexyl-[3,6-dimethoxy-2-[2,4,6-tri(propan-2-yl)phenyl]phenyl]phosphane methanesulfonic acid N-methyl-2-phenylaniline palladium / 1,4-dioxane / 48 h / 60 °C / Sealed tube; Inert atmosphere

Reference： [1]Current Patent Assignee: KALVISTA PHARMACEUTICALS INC - WO2022/175675, 2022, A1

14
[ 1638761-29-1 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 20 °C / Cooling with ice 2: potassium carbonate / acetonitrile / 72 h / 60 °C

Reference： [1]Current Patent Assignee: KALVISTA PHARMACEUTICALS INC - WO2022/175675, 2022, A1

15
[ 1638761-29-1 ]
[ 2824121-76-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 20 °C / Cooling with ice 2: potassium carbonate / acetonitrile / 72 h / 60 °C 3: hydrogenchloride / 1,4-dioxane / 20 h / 20 °C

Reference： [1]Current Patent Assignee: KALVISTA PHARMACEUTICALS INC - WO2022/175675, 2022, A1

16
[ 1638761-29-1 ]
[ 2824121-77-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: triethylamine / dichloromethane / 20 °C / Cooling with ice 2: potassium carbonate / acetonitrile / 72 h / 60 °C 3: hydrogenchloride / 1,4-dioxane / 20 h / 20 °C 4: Cs₂CO₃; dicyclohexyl-[3,6-dimethoxy-2-[2,4,6-tri(propan-2-yl)phenyl]phenyl]phosphane methanesulfonic acid N-methyl-2-phenylaniline palladium / 1,4-dioxane / 72 h / 60 °C / Sealed tube; Inert atmosphere

Reference： [1]Current Patent Assignee: KALVISTA PHARMACEUTICALS INC - WO2022/175675, 2022, A1

17
[ 1638761-29-1 ]
[ 91476-80-1 ]
[ 2824121-72-2 ]

Yield	Reaction Conditions	Operation in experiment
51%	Stage #1: tert-butyl N-[3-(hydroxymethyl)bicyclo[1.1.1]pentan-1-yl]methyl}carbamate With Dess-Martin periodane In dichloromethane at 20℃; for 3h; Cooling with ice; Stage #2: With Sodium hydrogenocarbonate; Na₂S₂O₃ for 0.25h; Stage #3: 5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine Further stages;	1004 Tert-butyl N-[[3-(6,8-dihydro-5H-imidazo[1,2-a]pyrazin-7-ylmethyl)-1- bicyclo[1.1.1]pentanyl]methyl]carbamate Tert-Butyl N-[3-(hydroxymethyl)bicyclo[1.1.1]pentan-1-yl]methyl}carbamate (100 mg, 0.44 mmol) was taken up in DCM (5 mL) while cooling in an ice/water bath. Dess-Martin periodinane (261 mg, 0.62 mmol) was added and the mixture stirred at rt for 3 h. Sat. Na2S2O3 (aq) (5 mL) and sat. NaHCO3 (aq) (5 mL), were added and the mixture stirred for 15 min and extracted with DCM (3 x 20 mL). The combined organics were washed with brine (10 mL), dried (MgSO4) and concentrated. The residue was suspended in THF (10 mL). 5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazine (60 mg, 0.48 mmol) was added and the reaction was stirred for 15 min. STAB (278 mg, 1.32 mmol) was added and the mixture was stirred at rt for 18 h. Water (10 mL) was added and the mixture extracted with DCM (3 x 10 mL). The combined organics were washed with brine (10 mL), dried (MgSO4) and concentrated. The residue was passed directly through an SCX and washed with MeOH. The product was eluted with a solution of 1M NH3 in MeOH and concentrated to afford the product (75 mg, 51% yield). [M+H]+ = 333.2
51%	Stage #1: tert-butyl N-[3-(hydroxymethyl)bicyclo[1.1.1]pentan-1-yl]methyl}carbamate With Dess-Martin periodane In dichloromethane at 20℃; for 3h; Cooling with ice; Stage #2: With Sodium hydrogenocarbonate; Na₂S₂O₃ for 0.25h; Stage #3: 5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine Further stages;	1004 Tert-butyl N-[[3-(6,8-dihydro-5H-imidazo[1,2-a]pyrazin-7-ylmethyl)-1- bicyclo[1.1.1]pentanyl]methyl]carbamate Tert-Butyl N-[3-(hydroxymethyl)bicyclo[1.1.1]pentan-1-yl]methyl}carbamate (100 mg, 0.44 mmol) was taken up in DCM (5 mL) while cooling in an ice/water bath. Dess-Martin periodinane (261 mg, 0.62 mmol) was added and the mixture stirred at rt for 3 h. Sat. Na2S2O3 (aq) (5 mL) and sat. NaHCO3 (aq) (5 mL), were added and the mixture stirred for 15 min and extracted with DCM (3 x 20 mL). The combined organics were washed with brine (10 mL), dried (MgSO4) and concentrated. The residue was suspended in THF (10 mL). 5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazine (60 mg, 0.48 mmol) was added and the reaction was stirred for 15 min. STAB (278 mg, 1.32 mmol) was added and the mixture was stirred at rt for 18 h. Water (10 mL) was added and the mixture extracted with DCM (3 x 10 mL). The combined organics were washed with brine (10 mL), dried (MgSO4) and concentrated. The residue was passed directly through an SCX and washed with MeOH. The product was eluted with a solution of 1M NH3 in MeOH and concentrated to afford the product (75 mg, 51% yield). [M+H]+ = 333.2

Reference： [1]Current Patent Assignee: KALVISTA PHARMACEUTICALS INC - WO2022/175675, 2022, A1 Location in patent: Page/Page column 459-460
[2]Current Patent Assignee: KALVISTA PHARMACEUTICALS INC - WO2022/175675, 2022, A1 Location in patent: Page/Page column 459-460

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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
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H221	Flammable gas
H222	Extremely flammable aerosol
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H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
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H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 1638761-29-1 ] {[proInfo.proName]}

Quality Control of [ 1638761-29-1 ]

Related Doc. of [ 1638761-29-1 ]

Product Details of [ 1638761-29-1 ]

Safety of [ 1638761-29-1 ]

Application In Synthesis of [ 1638761-29-1 ]

[ 1638761-29-1 ] Synthesis Path-Downstream 1~17

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