Piperazine → HCID 57563102, 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]([OH:14])=O)=[CH:10][CH:9]=1)#[N:2].[NH:41]1[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]1>>[C:1]([C:3]1[CH:4]=[C:5]([CH:38]=[CH:39][CH:40]=1)[CH2:6][N:7]([C:8]1[CH:16]=[CH:15][C:11]([C:12]([N:41]2[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]2)=[O:14])=[CH:10][CH:9]=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) (60 mg, 0.11 mmol) and piperazine (29 mg, 0.33 mmol) afforded COMPOUND 134 as a white solid (23 mg, 34%). 1H NMR (CDCl3) δ 0.98-1.18 (m, 2H), 1.01 (d, 3H, J=6.6 Hz), 1.51-1.55 (m, 1H), 1.70-1.82 (m, 3H), 2.18 (t, 1H, J=11.1 Hz), 2.31 (s, 6H), 2.58 (t, 1H, J=11.1 Hz), 2.76-2.92 (m, 7H), 3.26-3.33 (m, 1H), 3.58-3.72 (m, 5H), 3.87 (m, 3H), 6.51 (d, 2H, J=8.7 Hz), 6.95 (d, 2H, J=7.5 Hz), 7.03-7.08 (m, 1H), 7.23-7.26 (m, 2H), 7.42-7.47 (m, 3H), 7.55 (d, 1H, J=6.6 Hz), 8.26 (br s, 1H). 13C NMR (CDCl3) δ 13.82, 19.55, 29.41, 30.70, 31.42, 40.14, 43.98, 46.66, 48.43, 52.45, 56.42, 60.83, 112.64, 113.03, 119.29, 124.40, 127.70, 128.79, 129.72, 130.18, 131.01, 131.12, 134.51, 139.03, 141.94, 149.74, 170.22, 171.00. ES-MS m/z 607 (M+H). Anal. Calcd. for C37H46N6O2.CH2Cl2: C, 70.10; H, 7.36; N, 13.12. Found. C, 69.89; H, 7.48; N, 13.02.
Sources & evidence
- ORD record
- ord-ebb1f6c63b5d46638045be50140dffea
- Source dataset
- uspto-grants-2009_02
- Patent number
- US07491735B2
Reaction notes
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