Pyridine → Methyl 3-(3-((2-(4-(3,4-dimethylphenylamino)pyridin-2-yl)-4-(piperidin-1-yl)phenyl)carbamoyl)benzylthio)propanoate

HRID 625396Notes

Reaction equation

HRID 625396 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][C:3]=1[C:14]1[CH:19]=[C:18]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[C:23]([CH3:28])[CH:22]=2)[CH:17]=[CH:16][N:15]=1.N1C=CC=CC=1.Cl[C:36]([C:38]1[CH:39]=[C:40]([CH:49]=[CH:50][CH:51]=1)[CH2:41][S:42][CH2:43][CH2:44][C:45]([O:47][CH3:48])=[O:46])=[O:37]>O1CCCC1>[CH3:28][C:23]1[CH:22]=[C:21]([NH:20][C:18]2[CH:17]=[CH:16][N:15]=[C:14]([C:3]3[CH:4]=[C:5]([N:8]4[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]4)[CH:6]=[CH:7][C:2]=3[NH:1][C:36]([C:38]3[CH:39]=[C:40]([CH:49]=[CH:50][CH:51]=3)[CH2:41][S:42][CH2:43][CH2:44][C:45]([O:47][CH3:48])=[O:46])=[O:37])[CH:19]=2)[CH:26]=[CH:25][C:24]=1[CH3:27]

Participants

5

Reactant 3

HCID 1049PyridineHCID 665869052-(2-amino-5-(piperidin-1-yl)phenyl)-N-(3,4-dimethylphenyl)pyridin-4-amineHCID 86705202Methyl 3-(3-(chlorocarbonyl)benzylthio)propanoate

Product 1

HCID 66586906Methyl 3-(3-((2-(4-(3,4-dimethylphenylamino)pyridin-2-yl)-4-(piperidin-1-yl)phenyl)carbamoyl)benzylthio)propanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a 50-mL 3-necked round bottom flask, was placed a solution of 2-(2-amino-5-(piperidin-1-yl)phenyl)-N-(3,4-dimethylphenyl)pyridin-4-amine (270 mg, 0.72 mmol, 1.00 equiv) in tetrahydrofuran (10 mL), pyridine (170 mg, 2.15 mmol, 2.97 equiv), and methyl 3-(3-(chlorocarbonyl)benzylthio)propanoate (197.6 mg, 0.72 mmol, 1.00 equiv). The resulting solution was stirred for 1.5 h at room temperature. This reaction was used directly in next step without workup.

Workup

  1. customInto a 50-mL 3-necked round bottom flask, was placed

Sources & evidence

ORD record
ord-bf600369c3ee4deda99e841103b5a451
Source dataset
uspto-grants-2016_04
Patent number
US09301951B2

Reaction notes

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