Cyanoacetic acid → N-(3-(2-(4-morpholinophenylamino)pyrimidin-4-ylthio)phenyl)-2-cyanoacetamide

HRID 577409Notes

Reaction equation

HRID 577409 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([S:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)=[CH:18][CH:17]=3)[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[C:28]([CH2:30][C:31](O)=[O:32])#[N:29]>>[O:25]1[CH2:24][CH2:23][N:22]([C:19]2[CH:18]=[CH:17][C:16]([NH:15][C:11]3[N:10]=[C:9]([S:8][C:4]4[CH:3]=[C:2]([NH:1][C:31](=[O:32])[CH2:30][C:28]#[N:29])[CH:7]=[CH:6][CH:5]=4)[CH:14]=[CH:13][N:12]=3)=[CH:21][CH:20]=2)[CH2:27][CH2:26]1

Participants

3

Reactant 2

HCID 9740Cyanoacetic acidHCID 249899214-(3-aminophenylthio)-N-(4-morpholinophenyl)pyrimidin-2-amine

Product 1

HCID 24989919N-(3-(2-(4-morpholinophenylamino)pyrimidin-4-ylthio)phenyl)-2-cyanoacetamideYield 65.5%

Procedure

In a procedure analogous to Example 15, reaction of 4-(3-aminophenylthio)-N-(4-morpholinophenyl)pyrimidin-2-amine (50 mg, 0.13 mmol) and cyanoacetic acid (23 mg, 0.26 mmol) furnished the product (38 mg, 64%).

Sources & evidence

ORD record
ord-7fcfb379f94c44dab78b3b23420c7608
Source dataset
uspto-grants-2015_05
Patent number
US09040549B2

Reaction notes

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