Methylamine hydrochloride → HCID 57563192, 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](=[O:36])[C:28]2[C:33]([CH3:34])=[CH:32][CH:31]=[CH:30][C:29]=2[CH3:35])[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][NH2:43]>>[C:1]([C:3]1[CH:4]=[C:5]([CH:38]=[CH:39][CH:40]=1)[CH2:6][N:7]([C:8]1[CH:9]=[CH:10][C:11]([C:12](=[O:13])[NH:43][CH3:42])=[CH:15][CH:16]=1)[CH:17]1[CH2:18][CH2:19][N:20]([CH:23]([CH3:37])[CH2:24][CH2:25][NH:26][C:27](=[O:36])[C:28]2[C:33]([CH3:34])=[CH:32][CH:31]=[CH:30][C:29]=2[CH3:35])[CH2:21][CH2:22]1)#[N:2]Participants
Procedure
Using general procedure E, 4-((3-cyano-benzyl)-{1-[3-(2,6-dimethyl-benzoylamino)-1-methyl-propyl]-piperidin-4-yl}-amino)-benzoic acid (see EXAMPLE 131) (30 mg, 0.056 mmol) and methylamine hydrochloride (19 mg, 0.28 mmol) afforded COMPOUND 132 as a white solid (22 mg, 72%). 1H NMR (CDCl3) δ 1.01 (d, 3H, J=6.3 Hz), 1.15-1.26 (m, 1H), 1.52-1.75 (m, 4H), 2.15-2.37 (m, 2H), 2.31 (s, 6H), 2.59 (t, 1H, J=11.1 Hz), 2.76-2.88 (m, 3H), 2.96 (d, 3H, J=4.2 Hz), 3.20-3.33 (m, 1H), 3.67-3.74 (m, 1H), 3.85-3.89 (m, 1H), 3.89 (s, 2H), 5.91 (br s, 1H), 6.52 (d, 2H, J=8.4 Hz), 6.96 (d, 2H, J=7.2 Hz), 7.04-7.09 (m, 1H), 7.41-7.46 (m, 3H), 7.54-7.57 (m, 3H), 8.25 (br s, 1H). 13C NMR (CDCl3) δ 13.85, 19.54, 27.07, 29.47, 30.73, 31.40, 40.13, 43.97, 48.36, 52.39, 56.37, 60.80, 112.55, 113.05, 119.20, 123.36, 127.70, 128.80, 128.86, 129.76, 130.13, 131.07, 134.52, 139.01, 141.73, 150.81, 168.13, 170.24. ES-MS m/z 552 (M+H). Anal. Calcd. for C34H41N5O2.0.9H2O: C, 71.90; H, 7.60; N, 12.33. Found. C, 71.72; H, 7.71; N, 12.72.
Sources & evidence
- ORD record
- ord-9f40943f58f84d09a733ef411cc141b4
- Source dataset
- uspto-grants-2009_02
- Patent number
- US07491735B2
Reaction notes
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