4,6-Dimethylpyrimidine-5-carboxylic acid → HCID 68971776, compound

HRID 1726185Notes

Reaction equation

HRID 1726185 reaction equation
C[O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][C:7]([N:10]([CH:20]2[CH2:25][CH2:24][N:23]([CH:26]([CH3:30])[CH2:27][CH2:28][NH2:29])[CH2:22][CH2:21]2)[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]#[N:19])[CH:13]=2)=[CH:6][CH:5]=1.[CH3:32][C:33]1[C:38]([C:39]([OH:41])=O)=[C:37]([CH3:42])[N:36]=[CH:35][N:34]=1>>[C:18]([C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][CH:15]=1)[CH2:11][N:10]([CH:20]1[CH2:21][CH2:22][N:23]([CH:26]([CH3:30])[CH2:27][CH2:28][NH:29][C:39]([C:38]2[C:33]([CH3:32])=[N:34][CH:35]=[N:36][C:37]=2[CH3:42])=[O:41])[CH2:24][CH2:25]1)[C:7]1[CH:6]=[CH:5][C:4]([C:3]([OH:31])=[O:2])=[CH:9][CH:8]=1)#[N:19]

Participants

3

Reactant 2

HCID 149222224,6-Dimethylpyrimidine-5-carboxylic acidHCID 68968569HCID 68968569, compound

Product 1

HCID 68971776HCID 68971776, compoundYield 74%

Procedure

Using general procedure E with 4-[[1-(3-amino-1-methyl-propyl)-piperidin-4-yl]-(3-cyano-benzyl)-amino]-benzoic acid methyl ester (see EXAMPLE 107) (300 mg, 0.71 mmol) and 4,6-dimethyl-pyrimidine-5-carboxylic acid (119 mg, 0.78 mmol) followed by general procedure K with the resulting ester afforded 4-[(3-cyano-benzyl)-(1-{3-[(4,6-dimethyl-pyrimidine-5-carbonyl)-amino]-1-methyl-propyl}-piperidin-4-yl)-amino]-benzoic acid as a white solid (260 mg, 74%).

Sources & evidence

ORD record
ord-d94be538f98243deaac3da387dbe2ad4
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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