Glycine methyl ester hydrochloride → HCID 57563235, compound
Reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:38]=[CH:39][CH:40]=1)[CH2:6][N:7]([CH:17]1[CH2:22][CH2:21][N:20]([CH:23]([CH3:37])[CH2:24][CH2:25][NH:26][C:27]([C:29]2[C:30]([CH3:36])=[N:31][CH:32]=[N:33][C:34]=2[CH3:35])=[O:28])[CH2:19][CH2:18]1)[C:8]1[CH:16]=[CH:15][C:11]([C:12](O)=[O:13])=[CH:10][CH:9]=1)#[N:2].Cl.[CH3:42][O:43][C:44](=[O:47])[CH2:45][NH2:46]>>[CH3:42][O:43][C:44](=[O:47])[CH2:45][NH:46][C:12](=[O:13])[C:11]1[CH:15]=[CH:16][C:8]([N:7]([CH2:6][C:5]2[CH:38]=[CH:39][CH:40]=[C:3]([C:1]#[N:2])[CH:4]=2)[CH:17]2[CH2:22][CH2:21][N:20]([CH:23]([CH3:37])[CH2:24][CH2:25][NH:26][C:27]([C:29]3[C:34]([CH3:35])=[N:33][CH:32]=[N:31][C:30]=3[CH3:36])=[O:28])[CH2:19][CH2:18]2)=[CH:9][CH:10]=1Participants
Procedure
Using general procedure E, 4-[(3-cyano-benzyl)-(1-{3-[(4,6-dimethyl-pyrimidine-5-carbonyl)-amino]-1-methyl-propyl}-piperidin-4-yl)-amino]-benzoic acid (see EXAMPLE 129) (100 mg, 0.26 mmol) and glycine methyl ester hydrochloride (46 mg, 0.37 mmol) afforded COMPOUND 175 as a white solid (65 mg, 57%). 1H NMR (CDCl3) δ 1.04 (d, 3H, J=6.3 Hz), 1.04-1.26 (m, 2H), 1.46-1.62 (m, 1H), 1.67-1.86 (m, 3H), 2.14-2.27 (m, 1H), 2.51 (s, 6H), 2.56-2.65 (m, 1H), 2.70-2.93 (m, 3H), 3.28-3.38 (m, 2H), 3.47-3.53 (m, 1H), 3.67-3.89 (m, 2H), 3.96-4.07 (m, 3H), 4.20, 4.21 (s, 2H), 6.43-6.59 (m, 3H), 7.42-7.58 (m, 4H), 7.64 (d, 3H, J=8.1 Hz), 8.49 (br s, 1H), 8.90 (s, 1H). 13C NMR (CDCl3) δ 13.50, 14.75, 21.97, 25.65, 28.42, 29.32, 30.43, 30.82, 36.04, 36.33, 39.99, 41.65, 43.55, 44.41, 48.02, 51.89, 52.40, 53.80, 55.71, 56.68, 60.17, 111.77, 112.07, 112.78, 118.78, 122.09, 128.89, 129.50, 129.65, 130.72, 130.84, 131.65, 140.87, 150.78, 157.58, 158.34, 163.12, 166.28, 166.90, 170.80, 181.11. ES-MS m/z 612 (M+H).
Sources & evidence
- ORD record
- ord-49d20a63e17246589ef18a513e32a30a
- Source dataset
- uspto-grants-2009_02
- Patent number
- US07491735B2
Reaction notes
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