2-Chloro-6-methylbenzoic acid → HCID 57563040, compound
Reaction equation
C[O:2][C:3](=[O:38])[C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]([CH:27]3[CH2:32][CH2:31][N:30]([CH:33]([CH3:37])[CH2:34][CH2:35][NH2:36])[CH2:29][CH2:28]3)[CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]#[N:26])[CH:20]=3)=[CH:13][CH:12]=2)=[CH:6][CH:5]=1.[Cl:39][C:40]1[CH:48]=[CH:47][CH:46]=[C:45]([CH3:49])[C:41]=1[C:42](O)=[O:43]>>[Cl:39][C:40]1[CH:48]=[CH:47][CH:46]=[C:45]([CH3:49])[C:41]=1[C:42]([NH:36][CH2:35][CH2:34][CH:33]([N:30]1[CH2:29][CH2:28][CH:27]([N:17]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]#[N:26])[CH:20]=2)[C:14]2[CH:13]=[CH:12][C:11]([O:10][C:7]3[CH:6]=[CH:5][C:4]([C:3]([OH:2])=[O:38])=[CH:9][CH:8]=3)=[CH:16][CH:15]=2)[CH2:32][CH2:31]1)[CH3:37])=[O:43]Participants
Procedure
Using general procedure E with 4-{4-[[1-(3-amino-1-methyl-propyl)-piperidin-4-yl]-(3-cyano-benzyl)-amino]-phenoxy}-benzoic acid methyl ester (see EXAMPLE 162) (80 mg, 0.16 mmol) and 2-chloro-6-methyl benzoic acid (29 mg, 0.17 mmol) followed by general procedure K afforded COMPOUND 163 as a white solid (42 mg, 41% over 2 steps). 1H NMR (CD3OD) δ 1.39 (d, 3H, J=6.6 Hz), 1.79-2.07 (m, 3H), 2.08-2.21 (m, 3H), 2.34 (s, 3H), 3.06-3.26 (m, 2H), 3.34-3.64 (m, 5H), 3.98-4.10 (m, 1H), 4.48 (s, 2H), 6.86 (d, 2H, J=8.4 Hz), 6.92 (s, 4H), 7.19-7.30 (m, 3H), 7.44-7.51 (m, 1H), 7.55-7.65 (m, 3H), 7.91 (d, 2H, J=8.4 Hz). 13C NMR (CD3OD) δ 14.26, 19.87, 28.36, 28.48, 32.53, 37.62, 51.11, 56.02, 61.37, 113.82, 117.65, 119.02, 120.25, 122.79, 128.23, 128.90, 130.28, 131.07, 131.75, 131.85, 131.92, 132.11, 133.03, 133.18, 138.02, 138.59, 143.83, 146.92, 149.84, 163.81, 171.08, 172.17. ES-MS m/z 651 (M+H). Anal. Calcd. for C38H39N4ClO4.0.5CH2Cl2.1.7H2O: C, 63.84; H, 6.04; N, 7.74; Cl, 9.79. Found. C, 63.70; H, 6.08; N, 7.64; Cl, 9.92.
Sources & evidence
- ORD record
- ord-1ae94448a41140ff8deea21d016654c6
- Source dataset
- uspto-grants-2009_02
- Patent number
- US07491735B2
Reaction notes
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