2,6-Dimethylbenzoic acid → HCID 57563261, compound

HRID 1726231Notes

Reaction equation

HRID 1726231 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[CH:49]=[CH:48][CH:47]=[C:46]([CH3:50])[C:42]=1[C:43](O)=[O:44]>>[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[CH2:33][CH2:32][N:31]([CH:34]([CH3:38])[CH2:35][CH2:36][NH:37][C:43](=[O:44])[C:42]2[C:46]([CH3:50])=[CH:47][CH:48]=[CH:49][C:41]=2[CH3:40])[CH2:30][CH2:29]1)[C:14]1[CH:15]=[CH:16][C:11]([O:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:2])=[O:39])=[CH:5][CH:6]=2)=[CH:12][CH:13]=1)#[N:26]

Participants

3

Reactant 2

HCID 124392,6-Dimethylbenzoic acidHCID 68970484HCID 68970484, compound

Product 1

HCID 57563261HCID 57563261, compound

Procedure

Using general procedure E with 4-{4-[[1-(3-amino-1-methyl-propyl)-piperidin-4-yl]-(5-cyano-2-fluoro-benzyl)-amino]-phenoxy}-benzoic acid methyl ester (see EXAMPLE 228) (90 mg, 0.17 mmol) and 2,6-dimethylbenzoic acid (29 mg, 0.19 mmol) followed by general procedure K with the resulting ester afforded COMPOUND 229 as a white solid (58 mg, 53% over 2 steps). 1H NMR (CDCl3) δ 1.06-1.16 (m, 3H), 1.53-1.69 (m, 1H), 1.78-2.04 (m, 3H), 2.28 (s, 6H), 2.32-2.45 (m, 1H), 2.63-2.75 (m, 1H), 2.92-3.18 (m, 3H), 3.29-3.45 (m, 2H), 3.57-3.82 (m, 3H), 4.11 (s, 2H), 6.58-6.65 (m, 2H), 6.82-7.03 (m, 7H), 7.12-7.21 (m, 1H), 7.50-7.85 (m, 2H), 7.79-8.01 (m, 3H). 13C NMR (CDCl3) δ 11.81, 18.19, 26.45, 27.05, 30.35, 36.88, 42.30, 43.32, 49.61, 55.06, 57.96, 107.47, 114.99, 115.37, 115.81, 117.29, 120.17, 125.91, 126.28, 127.40, 128.17 (d, J=15 Hz), 130.59, 131.94, 132.92, 136.93, 143.59, 147.04, 160.57, 161.58 (d, J=256 Hz), 169.66, 170.16. ES-MS m/z 649 (M+H). Anal. Calcd. for C39H41N4O4F.0.9CH2Cl2: C, 66.08; H, 5.95; N, 7.73; F, 2.62. Found: C, 66.11; H, 6.08; N, 7.64; F, 2.48.

Sources & evidence

ORD record
ord-a78f5fdcabd64ee98fd2bc2d9c1d4984
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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