[ CAS No. 1375465-91-0 ] {[proInfo.proName]}

Name: 1375465-91-0|N-Hydroxy-2-((1-phenylcyclopropyl)amino)pyrimidine-5-carboxamide|98%
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SKU: A213388
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Quality Control of [ 1375465-91-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1375465-91-0 ]

SDS Specification

Alternatived Products of [ 1375465-91-0 ]

Product Details of [ 1375465-91-0 ]

CAS No. :	1375465-91-0	MDL No. :	MFCD28347706
Formula :	C₁₄H₁₄N₄O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LIIWIMDSZVNYHY-UHFFFAOYSA-N
M.W :	270.29	Pubchem ID :	57381425
Synonyms :

Calculated chemistry of [ 1375465-91-0 ]

Physicochemical Properties

Num. heavy atoms :	20
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.21
Num. rotatable bonds :	5
Num. H-bond acceptors :	4.0
Num. H-bond donors :	3.0
Molar Refractivity :	72.13
TPSA :	87.14 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.13 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.08
Log Po/w (XLOGP3) :	1.15
Log Po/w (WLOGP) :	1.33
Log Po/w (MLOGP) :	1.13
Log Po/w (SILICOS-IT) :	1.18
Consensus Log Po/w :	1.37

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.35
Solubility :	1.2 mg/ml ; 0.00442 mol/l
Class :	Soluble
Log S (Ali) :	-2.57
Solubility :	0.72 mg/ml ; 0.00266 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.47
Solubility :	0.00924 mg/ml ; 0.0000342 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.05

Safety of [ 1375465-91-0 ]

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 [ 1375465-91-0 ]

* 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.

Downstream synthetic route of [ 1375465-91-0 ]

[ 1375465-91-0 ] Synthesis Path-Downstream 1~1

1
[ 1598426-03-9 ]
[ 1375465-91-0 ]

Yield	Reaction Conditions	Operation in experiment
79%	With hydroxylamine hydrochloride; sodium methylate In methanol at 10℃; for 2h;	4 Synthesis of N-hydroxy-2-((1-phenylcyclopropyl)amino)pyrimidine-5-carboxamide (Compound D) [0253] A solution of MeOH (1000 ml) was cooled to about 0-5° C. with stirring. NH2OH HCl (1107 g, 10 equiv.) was added, followed by careful addition of NaOCH3 (1000 g, 12.0 equiv.) The resulting mixture was stirred at 0-5° C. for one hr, and was filtered to remove the solid. Compound 4 (450 g, 1.0 equiv.) was added to the reaction mixture in one portion, and stirred at 10° C. for two hours until compound 4 was consumed. The reaction mixture was adjusted to a pH of about 8.5-9 through addition of HCl (6N), resulting in precipitation. The mixture was concentrated under reduced pressure. Water (3000 ml) was added to the residue with intense stirring and the precipitate was collected by filtration. The product was dried in an oven at 45° C. overnight (340 g, 79% yield).
79%	With hydroxylamine hydrochloride; sodium methylate In methanol at 10℃; for 2h;	4 Synthesis of N-hydroxy-2-((1-phenylcyclopropyl)amino)pyrimidine-5-carboxamide (Compound D) Synthesis of N-hydroxy-2-((1-phenylcyclopropyl)amino)pyrimidine-5-carboxamide (Compound D) A solution of MeOH (1000 ml) was cooled to about 0-5° C. with stirring. NH2OH HCl (1107 g, 10 equiv.) was added, followed by careful addition of NaOCH3 (1000 g, 12.0 equiv.) The resulting mixture was stirred at 0-5° C. for one hr, and was filtered to remove the solid. Compound 4 (450 g, 1.0 equiv.) was added to the reaction mixture in one portion, and stirred at 10° C. for two hours until compound 4 was consumed. The reaction mixture was adjusted to a pH of about 8.5-9 through addition of HCl (6N), resulting in precipitation. The mixture was concentrated under reduced pressure. Water (3000 ml) was added to the residue with intense stirring and the precipitate was collected by filtration. The product was dried in an oven at 45° C. overnight (340 g, 79% yield).
79%	With hydroxylamine hydrochloride; sodium methylate In methanol at 10℃; for 2h;	4.D Synthesis of N-hydroxy-2-((1-phenylcyclopropyl)amino)pyrimidine-5-carboxamide (Compound D) Synthesis of N-hydroxy-2-((1-phenylcyclopropyl)amino)pyrimidine-5-carboxamide (Compound D) A solution of MeOH (1000 ml) was cooled to about 0-5° C. with stirring. NH2OH HCl (1107 g, 10 equiv.) was added, followed by careful addition of NaOCH3 (1000 g, 12.0 equiv.) The resulting mixture was stirred at 0-5° C. for one hr, and was filtered to remove the solid. Compound 4 (450 g, 1.0 equiv.) was added to the reaction mixture in one portion, and stirred at 10° C. for two hours until compound 4 was consumed. The reaction mixture was adjusted to a pH of about 8.5-9 through addition of HCl (6N), resulting in precipitation. The mixture was concentrated under reduced pressure. Water (3000 ml) was added to the residue with intense stirring and the precipitate was collected by filtration. The product was dried in an oven at 45° C. overnight (340 g, 79% yield).

79%	With hydroxylamine hydrochloride; sodium methylate In methanol at 10℃; for 2h;	4.D Synthesis of N-hydroxy-2-((1-phenylcyclopropyl)amino)pyrimidine-5-carboxamide (Compound D) A solution of MeOH (1000 ml) was cooled to about 0-5° C. with stirring. NH2OH HCl (1107 g, 10 equiv.) was added, followed by careful addition of NaOCH3 (1000 g, 12.0 equiv.) The resulting mixture was stirred at 0-5° C. for one hr, and was filtered to remove the solid. Compound 4 (450 g, 1.0 equiv.) was added to the reaction mixture in one portion, and stirred at 10° C. for two hours until compound 4 was consumed. The reaction mixture was adjusted to a pH of about 8.5-9 through addition of HCl (6N), resulting in precipitation. The mixture was concentrated under reduced pressure. Water (3000 ml) was added to the residue with intense stirring and the precipitate was collected by filtration. The product was dried in an oven at 45° C. overnight (340 g, 79% yield).
79%	With hydroxylamine hydrochloride; sodium methylate In methanol at 0 - 10℃; for 3h;	4 Synthesis of N-hydroxy-2-((1-phenylcyclopropyl)amino)pyrimidine-5-carboxamide (Compound D) Synthesis of N-hydroxy-2-((1-phenylcyclopropyl)amino)pyrimidine-5-carboxamide (Compound D) A solution of MeOH (1000 ml) was cooled to about 0-5° C. with stirring. NH2OH HCl (1107 g, 10 equiv.) was added, followed by careful addition of NaOCH3 (1000 g, 12.0 equiv.) The resulting mixture was stirred at 0-5° C. for one hr, and was filtered to remove the solid. Compound 4 (450 g, 1.0 equiv.) was added to the reaction mixture in one portion, and stirred at 10° C. for two hours until compound 4 was consumed. The reaction mixture was adjusted to a pH of about 8.5-9 through addition of HCl (6N), resulting in precipitation. The mixture was concentrated under reduced pressure. Water (3000 ml) was added to the residue with intense stirring and the precipitate was collected by filtration. The product was dried in an oven at 45° C. overnight (340 g, 79% yield).
79%	With hydroxylamine hydrochloride; sodium methylate In methanol at 0 - 10℃; for 2h;	4 Synthesis o fN-hydroxy-2-(( 1 -phenylcyclopropyl)amino)pyrimidine-5 -carboxamide (Compound D): (Compound D): A solution of MeOH(1000 ml) was cooled to about 0-5 °C with stirring.NH2OH HC1 (1107 g, 10 equiv.) was added, followed by careful addition ofNaOCH3 (1000 g, 12.0 equiv.) The resulting mixture was stirred at 0-5 °C for one hr, and was filtered to remove the solid. Compound 4 (450 g, 1.0 equiv.) was added to the reaction mixture in one portion, and stirred at 10 °C for two hours until compound 4 was consumed. The reactionmixture was adjusted to a pH of about 8.5-9 through addition of HC1 (6N), resulting in precipitation. The mixture was concentrated under reduced pressure. Water (3000 ml) was added to the residue with intense stirring and the precipitate was collected by filtration. The product was dried in an oven at 45 °C overnight (340 g, 79% yield).
79%	With hydroxylamine hydrochloride; sodium methylate In methanol at 0 - 10℃;	1 Synthesis of N-hvdroxy-2-((l-phenylcvclopropyl)amino)pyrimidine-5-carboxamide (Compound A): Synthesis of N-hvdroxy-2-((l-phenylcvclopropyl)amino)pyrimidine-5-carboxamide (Compound A): A solution of MeOH(1000 ml) was cooled to about 0-5 °C with stirring. NH2OH HC1 (1107 g, 10 equiv.) was added, followed by careful addition of NaOCH3 (1000 g, 12.0 equiv.) The resulting mixture was stirred at 0-5 °C for one hr, and was filtered to remove the solid. Compound 4 (450 g, 1.0 equiv.) was added to the reaction mixture in one portion, and stirred at 10 °C for two hours until compound 4 was consumed. The reaction mixture was adjusted to a pH of about 8.5-9 through addition of HC1 (6N), resulting in precipitation. The mixture was concentrated under reduced pressure. Water (3000 ml) was added to the residue with intense stirring and the precipitate was collected by filtration. The product was dried in an oven at 45 °C overnight (340 g, 79% yield).
79%	With hydroxylamine hydrochloride; sodium methylate In methanol at 10℃; for 2h;	4 Synthesis of N-hydroxy-2-(( 1 -phenylcyclopropyl)amino)pyrimidine-5 -carboxamide(Comnound D: A solution of MeOH(1000 ml) was cooled to about 0-5 °C with stirring.NH2OH HC1 (1107 g, 10 equiv.) was added, followed by careful addition of NaOCH3 (1000 g, 12.0 equiv.) The resulting mixture was stirred at 0-5 °C for one hr, and was filtered to remove the solid. Compound 4 (450 g, 1.0 equiv.) was added to the reaction mixture in one portion, and stirred at 10 °C for two hours until compound 4 was consumed. The reaction mixture was adjusted to a pH of about 8.5-9 through addition of HC1 (6N), resulting inprecipitation. The mixture was concentrated under reduced pressure. Water (3000 ml) was added to the residue with intense stirring and the precipitate was collected by filtration. The product was dried in an oven at 45 °C overnight (340 g, 79% yield).
79%	With hydroxylamine hydrochloride; sodium methylate In methanol at 0 - 10℃; for 2h;	1.A Synthesis of N-hydroxy-2-((1-phenylcyclopropyl)amino)pyrimidine-5-carboxamide (Compound 1) 0120] A solution of MeOH (1000 mL) was cooled to about 0-5°C with stirring. NH2OH HCl (1107 g, 10 equiv) was added, followed by careful addition of NaOCH3 (1000 g, 12.0 equiv) The resulting mixture was stirred at 0-5°C for one hour and was filtered to remove the solid. Intermediate 4 (450 g, 1.0 equiv) was added to the reaction mixture in one portion and stirred at 10°C for two hours until intermediate 4 was consumed. The reaction mixture was adjusted to a pH of about 8.5-9 through addition of HCl (6N), resulting in precipitation. The mixture was concentrated under reduced pressure. Water (3000 mL) was added to the residue with intense stirring and the precipitate was collected by filtration. The product was dried in an oven at 45°C overnight (340 g, 79% yield).
79%	With hydroxylamine hydrochloride; sodium methylate In methanol at 0 - 10℃; for 3h;	14 Synthesis of N-hydroxy-2-((l-phenylcyclopropyl)amino)pyrimidine-5-carboxamide ( Compound D) A solution of MeOH(1000 ml) was cooled to about 0-5 °C with stirring. NH2OH HC1 (1107 g, 10 equiv.) was added, followed by careful addition of NaOCH3 (1000 g, 12.0 equiv.) The resulting mixture was stirred at 0-5 °C for one hr, and was filtered to remove the solid. Compound 4 (450 g, 1.0 equiv.) was added to the reaction mixture in one portion, and stirred at 10 °C for two hours until compound 4 was consumed. The reaction mixture was adjusted to a pH of about 8.5-9 through addition of HC1 (6N), resulting in precipitation. The mixture was concentrated under reduced pressure. Water (3000 ml) was added to the residue with intense stirring and the precipitate was collected by filtration. The product was dried in an oven at 45 °C overnight (340 g, 79% yield).
79%	With hydroxylamine hydrochloride; sodium methylate In methanol at 10℃; for 2h;	4 Synthesis of N-hvdroxy-2-((l-phenylcvclopropyl)amino)pyrimidine-5-carboxamide (Compound D) A solution of MeOH(1000 ml) was cooled to about 0-5 °C with stirring. H2OH HC1 (1107 g, 10 equiv.) was added, followed by careful addition of NaOCH3 (1000 g, 12.0 equiv.) The resulting mixture was stirred at 0-5 °C for one hr., and was filtered to remove the solid. Compound 4 (450 g, 1.0 equiv.) was added to the reaction mixture in one portion, and stirred at 10 °C for two hours until compound 4 was consumed. The reaction mixture was adjusted to a pH of about 8.5-9 through addition of HC1 (6N), resulting in precipitation. The mixture was concentrated under reduced pressure. Water (3000 ml) was added to the residue with intense stirring and the precipitate was collected by filtration. The product was dried in an oven at 45 °C overnight (340 g, 79% yield)
79%	With hydroxylamine hydrochloride; sodium methylate In methanol at 10℃; for 2h;	4 Synthesis of N-hydroxy-2-((1-phenylcyclopropyl)amino)pyrimidine-5-carboxamide (Compound D) A solution of MeOH(1000 ml) was cooled to about 0-5 °C with stirring. H2OH HCl (1107 g, 10 equiv.) was added, followed by careful addition of NaOCH3 (1000 g, 12.0 equiv.) The resulting mixture was stirred at 0-5 °C for one hr, and was filtered to remove the solid. Compound 4 (450 g, 1.0 equiv.) was added to the reaction mixture in one portion, and stirred at 10 °C for two hours until compound 4 was consumed. The reaction mixture was adjusted to a pH of about 8.5-9 through addition of HC1 (6N), resulting in precipitation. The mixture was concentrated under reduced pressure. Water (3000 ml) was added to the residue with intense stirring and the precipitate was collected by filtration. The product was dried in an oven at 45 °C overnight (340 g, 79% yield).

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2015/99744, 2015, A1 Location in patent: Paragraph 0253
[2]Current Patent Assignee: DANA-FARBER CANCER INSTITUTE; BRISTOL-MYERS SQUIBB CO - US2015/105358, 2015, A1 Location in patent: Paragraph 0413
[3]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2015/105409, 2015, A1 Location in patent: Paragraph 0221
[4]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2015/105383, 2015, A1 Location in patent: Paragraph 0233
[5]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2015/150871, 2015, A1 Location in patent: Paragraph 0271
[6]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2016/7423, 2016, A1 Location in patent: Page/Page column 42
[7]Current Patent Assignee: REGENACY PHARMACEUTICALS LLC - WO2016/90230, 2016, A1 Location in patent: Page/Page column 20
[8]Current Patent Assignee: UNIVERSITY OF MODENA AND REGGIO EMILIA - WO2016/87950, 2016, A1 Location in patent: Page/Page column 30
[9]Current Patent Assignee: REGENACY PHARMACEUTICALS LLC; BRISTOL-MYERS SQUIBB CO - US2017/114023, 2017, A1 Location in patent: Paragraph 0117; 0120
[10]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2017/143237, 2017, A1 Location in patent: Paragraph 53; 54
[11]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; H. LEE MOFFITT CANCER CENTER & RESEARCH INSTITUTE - WO2017/184774, 2017, A1 Location in patent: Page/Page column 48; 49
[12]Current Patent Assignee: DANA-FARBER CANCER INSTITUTE - WO2017/214565, 2017, A1 Location in patent: Page/Page column 38; 39

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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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H220	Extremely flammable gas
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
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H242	Heating may cause a fire
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H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
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Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
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H311	Toxic in contact with skin
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H315	Causes skin irritation
H316	Causes mild skin irritation
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H319	Causes serious eye irritation
H320	Causes eye irritation
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H331	Toxic if inhaled
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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. 1375465-91-0 ] {[proInfo.proName]}

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