Ammonium Chloride → HCID 11399155, compound

HRID 1726167Notes

Reaction equation

HRID 1726167 reaction equation
[CH2:1]([N:8]([CH:18]1[CH2:23][CH2:22][N:21]([CH:24]([CH3:44])[CH2:25][CH2:26][NH:27][C:28](=[O:43])[C:29]2[C:34]([CH3:35])=[CH:33][C:32]([C:36]3[CH:41]=[CH:40][N:39]=[CH:38][CH:37]=3)=[CH:31][C:30]=2[CH3:42])[CH2:20][CH2:19]1)[C:9]1[CH:17]=[CH:16][C:12]([C:13](O)=[O:14])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+:46]>>[CH2:1]([N:8]([C:9]1[CH:17]=[CH:16][C:12]([C:13](=[O:14])[NH2:46])=[CH:11][CH:10]=1)[CH:18]1[CH2:23][CH2:22][N:21]([CH:24]([CH3:44])[CH2:25][CH2:26][NH:27][C:28](=[O:43])[C:29]2[C:34]([CH3:35])=[CH:33][C:32]([C:36]3[CH:37]=[CH:38][N:39]=[CH:40][CH:41]=3)=[CH:31][C:30]=2[CH3:42])[CH2:20][CH2:19]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 25517Ammonium ChlorideHCID 68974542HCID 68974542, compound

Product 1

HCID 11399155HCID 11399155, compoundYield 72.9%

Procedure

Using general procedure E, 4-(benzyl-{1-[3-(2,6-dimethyl-4-pyridin-4-yl-benzoylamino)-1-methyl-propyl]-piperidin-4-yl}-amino)-benzoic acid (see EXAMPLE 91) (60 mg, 0.10 mmol) and ammonium chloride (22 mg, 0.41 mmol) afforded COMPOUND 92 as a white solid (43 mg, 71%). 1H NMR (CDCl3) δ 1.02 (d, 3H, J=5.7 Hz), 1.06-1.35 (m, 2H), 1.51-1.62 (m, 1H), 1.69-1.86 (m, 3H), 2.13-2.31 (m, 1H), 2.40 (s, 6H), 2.52-2.63 (m, 1H), 2.73-2.94 (m, 3H), 3.20-3.40 (m, 2H), 3.62-3.71 (m, 1H), 3.89 (s, 2H), 5.79 (br s, 2H), 6.49 (d, 2H, J=8.1 Hz), 6.84-6.93 (m, 2H), 7.12-7.22 (m, 3H), 7.25-7.33 (m, 2H), 7.41-7.48 (m, 2H), 7.57 (d, 2H, J=8.1 Hz), 8.20 (br s, 1H), 8.60-8.67 (m, 2H). 13C NMR (CDCl3) δ 13.45, 19.34, 29.05, 30.40, 31.30, 39.60, 43.73, 48.18, 51.98, 55.72, 60.12, 111.66, 120.60, 121.49, 125.76, 126.06, 126.75, 128.51, 129.11, 135.24, 138.06, 139.02, 139.21, 147.61, 150.35, 151.34, 169.08, 169.34. ES-MS m/z 590 (M+H).

Sources & evidence

ORD record
ord-a84b5dfc47e6444f88acee5efb8e0dd3
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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