4,6-Dimethylpyrimidine-5-carboxylic acid → HCID 57563217, compound
Reaction equation
C[O:2][C:3](=[O:39])[C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]([CH:28]3[CH2:33][CH2:32][N:31]([CH:34]([CH3:38])[CH2:35][CH2:36][NH2:37])[CH2:30][CH2:29]3)[CH2:18][C:19]3[CH:24]=[C:23]([C:25]#[N:26])[CH:22]=[CH:21][C:20]=3[F:27])=[CH:13][CH:12]=2)=[CH:6][CH:5]=1.[CH3:40][C:41]1[C:46]([C:47]([OH:49])=O)=[C:45]([CH3:50])[N:44]=[CH:43][N:42]=1>>[C:25]([C:23]1[CH:22]=[CH:21][C:20]([F:27])=[C:19]([CH:24]=1)[CH2:18][N:17]([CH:28]1[CH2:29][CH2:30][N:31]([CH:34]([CH3:38])[CH2:35][CH2:36][NH:37][C:47]([C:46]2[C:41]([CH3:40])=[N:42][CH:43]=[N:44][C:45]=2[CH3:50])=[O:49])[CH2:32][CH2:33]1)[C:14]1[CH:13]=[CH:12][C:11]([O:10][C:7]2[CH:6]=[CH:5][C:4]([C:3]([OH:39])=[O:2])=[CH:9][CH:8]=2)=[CH:16][CH:15]=1)#[N:26]Participants
Procedure
Using general procedure E with the above amine (90 mg, 0.17 mmol) and 4,6-dimethyl-pyrimidine-5-carboxylic acid (29 mg, 0.19 mmol) and then using general procedure K with the resulting ester afforded COMPOUND 228 as a white solid (40 mg, 36% over 2 steps). 1H NMR (CDCl3) δ 1.14-1.26 (m, 3H), 1.67-2.19 (m, 4H), 2.40-2.59 (m, 1H), 2.48 (s, 6H), 2.73-2.85 (m, 1H), 3.01-3.17 (m, 3H), 3.32-3.36 (m, 2H), 3.38-3.51 (m, 1H), 3.58-3.75 (m, 2H), 4.20-4.35 (m, 2H), 6.69 (d, 2H, J=8.4 Hz), 6.82-6.92 (m, 4H), 7.10-7.18 (m, 1H), 7.49-7.61 (m, 2H), 7.71 (d, 2H, J=7.8 Hz), 8.41 (br s, 1H), 8.87 (s, 1H). 13C NMR (CDCl3) δ 12.80, 22.42, 27.60, 28.02, 32.11, 38.06, 44.46, 51.32, 53.84, 56.22, 58.67, 108.95, 116.92, 117.30, 118.65, 121.60, 127.77, 129.38 (d, J=15 Hz), 130.85, 131.82, 133.35, 144.82, 148.94, 157.73, 161.83, 163.01 (d, J=256 Hz), 163.50, 167.60, 171.81. ES-MS m/z 651 (M+H). Anal. Calcd. for C37H39N6O4F.1.1CH2Cl2: C, 61.49; H, 5.58; N, 11.29; F, 2.55. Found: C, 61.44; H, 5.70; N, 11.14; F, 2.38.
Sources & evidence
- ORD record
- ord-9886b147f8f047e3bc28ca296091e398
- Source dataset
- uspto-grants-2009_02
- Patent number
- US07491735B2
Reaction notes
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