4,6-Dimethylpyrimidine-5-carboxylic acid → HCID 57563013, compound

HRID 1726172Notes

Reaction equation

HRID 1726172 reaction equation
C[O:2][C:3](=[O:36])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]([CH:25]3[CH2:30][CH2:29][N:28]([CH:31]([CH3:35])[CH2:32][CH2:33][NH2:34])[CH2:27][CH2:26]3)[CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:13][CH:12]=2)=[CH:6][CH:5]=1.[CH3:37][C:38]1[C:43]([C:44]([OH:46])=O)=[C:42]([CH3:47])[N:41]=[CH:40][N:39]=1>>[CH2:18]([N:17]([CH:25]1[CH2:30][CH2:29][N:28]([CH:31]([CH3:35])[CH2:32][CH2:33][NH:34][C:44]([C:43]2[C:38]([CH3:37])=[N:39][CH:40]=[N:41][C:42]=2[CH3:47])=[O:46])[CH2:27][CH2:26]1)[C:14]1[CH:15]=[CH:16][C:11]([CH2:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:36])=[O:2])=[CH:5][CH:6]=2)=[CH:12][CH:13]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 149222224,6-Dimethylpyrimidine-5-carboxylic acidHCID 68970507HCID 68970507, compound

Product 1

HCID 57563013HCID 57563013, compoundYield 70%

Procedure

Using general procedure E with 4-(4-{[1-(3-amino-1-methyl-propyl)-piperidin-4-yl]-benzyl-amino}-benzyl)-benzoic acid methyl ester (see EXAMPLE 100) (79 mg, 0.16 mmol) and 4,6-dimethyl-pyrimidine-5-carboxylic acid (30 mg, 0.20 mmol) followed by general procedure K with the resulting ester gave COMPOUND 102 as a yellow powder (59 mg, 70% over 2 steps). 1H NMR (CDCl3+CD3OD) δ 1.20 (d, 3H, J=6.0 Hz), 1.68 (m, 1H), 1.90 (m, 4H), 2.13 (m, 1H), 2.40 (s, 6H), 2.61 (m, 1H), 2.81 (m, 1H), 3.09-3.37 (m, 4H), 3.54 (m, 1H), 3.80 (m, 3H), 4.23 (s, 2H), 6.55 (d, 2H, J=7.8 Hz), 6.90 (d, 2H, J=7.8 Hz), 7.09 (m, 7H), 7.71 (d, 2H, J=7.5 Hz), 8.77 (s, 1H). 1H NMR (CDCl3+CD3OD) δ 12.71, 21.99, 27.18, 27.54, 31.62, 37.35, 41.10, 45.34, 50.14, 51.13, 54.40, 58.93, 114.26, 126.48, 126.91, 128.73, 128.87, 129.96, 130.02, 130.82, 131.69, 140.33, 146.24, 147.43, 157.34, 163.70, 167.59, 172.17. ES-MS m/z 606 (M+H). Anal. Calcd. for C37H43N5O3.0.7CH2Cl2: C, 68.07; H, 6.73; N, 10.53. Found. C, 68.09; H, 6.66; N, 10.49.

Sources & evidence

ORD record
ord-45ce078f2615480da0412eb5d7a4e5a7
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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