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

HRID 1726188Notes

Reaction equation

HRID 1726188 reaction equation
[CH3:1][C:2]1[C:7]([C:8]([OH:10])=O)=[C:6]([CH3:11])[N:5]=[CH:4][N:3]=1.C[O:13][C:14](=[O:42])[C:15]1[CH:20]=[CH:19][C:18]([N:21]([CH:31]2[CH2:36][CH2:35][N:34]([CH:37]([CH3:41])[CH2:38][CH2:39][NH2:40])[CH2:33][CH2:32]2)[CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]#[N:30])[CH:24]=2)=[CH:17][CH:16]=1>>[C:29]([C:25]1[CH:24]=[C:23]([CH:28]=[CH:27][CH:26]=1)[CH2:22][N:21]([CH:31]1[CH2:32][CH2:33][N:34]([CH:37]([CH3:41])[CH2:38][CH2:39][NH:40][C:8]([C:7]2[C:2]([CH3:1])=[N:3][CH:4]=[N:5][C:6]=2[CH3:11])=[O:10])[CH2:35][CH2:36]1)[C:18]1[CH:17]=[CH:16][C:15]([C:14]([OH:42])=[O:13])=[CH:20][CH:19]=1)#[N:30]

Participants

3

Reactant 2

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

Product 1

HCID 68971776HCID 68971776, compound

Procedure

Using general procedure E with 4,6-dimethyl-pyrimidine-5-carboxylic acid (71 mg, 0.46 mmol) and 4-[[1-(3-amino-1-methyl-propyl)-piperidin-4-yl]-(3-cyano-benzyl)-amino]-benzoic acid methyl ester (see EXAMPLE 107) (130 mg, 0.31 mmol) followed by general procedure K with the resulting ester gave 4-[(3-cyano-benzyl)-(1-{3-[(4,6-dimethyl-pyrimidine-5-carbonyl)-amino]-1-methyl-propyl}-piperidin-4-yl)-amino]-benzoic acid as a brown solid (105 mg, 64% over 2 steps).

Sources & evidence

ORD record
ord-173750f6dcb540518d6f70a6d40c0393
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

Loading…