Dimethylamine → HCID 11421806, compound

HRID 1726162Notes

Reaction equation

HRID 1726162 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:37]=[CH:38][CH:39]=1)[CH2:5][N:6]([CH:16]1[CH2:21][CH2:20][N:19]([CH:22]([CH3:36])[CH2:23][CH2:24][NH:25][C:26](=[O:35])[C:27]2[C:32]([CH3:33])=[CH:31][CH:30]=[CH:29][C:28]=2[CH3:34])[CH2:18][CH2:17]1)[C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=1.[CH3:40][NH:41][CH3:42]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:37]=[CH:38][CH:39]=1)[CH2:5][N:6]([C:7]1[CH:8]=[CH:9][C:10]([C:11](=[O:13])[N:41]([CH3:42])[CH3:40])=[CH:14][CH:15]=1)[CH:16]1[CH2:21][CH2:20][N:19]([CH:22]([CH3:36])[CH2:23][CH2:24][NH:25][C:26](=[O:35])[C:27]2[C:28]([CH3:34])=[CH:29][CH:30]=[CH:31][C:32]=2[CH3:33])[CH2:18][CH2:17]1

Participants

3

Reactant 2

HCID 674DimethylamineHCID 68973007HCID 68973007, compound

Product 1

HCID 11421806HCID 11421806, compoundYield 73.9%

Procedure

Using general procedure E, 4-((3-chloro-benzyl)-{1-[3-(2,6-dimethyl-benzoylamino)-1-methyl-propyl]-piperidin-4-yl}-amino)-benzoic acid (see EXAMPLE 86) (40 mg, 0.074) and dimethylamine (2.0M in THF, 56 μL, 0.11 mmol) afforded COMPOUND 87 as a white solid (31 mg, 71%). 1H NMR (CDCl3) δ 0.89-1.20 (m, 2H), 1.00 (d, 3H, J=6.3 Hz), 1.50-1.54 (m, 1H), 1.70-1.83 (m, 3H), 2.16 (t, 1H, J=11.1 Hz), 2.30 (s, 6H), 2.56 (t, 1H, J=12.0 Hz), 2.74-2.90 (m, 3H), 3.03 (s, 6H), 3.24-3.31 (m, 1H), 3.62-3.69 (m, 1H), 3.81 (s, 2H), 3.84-3.91 (m, 1H), 6.52 (d, 2H, J=8.4 Hz), 6.96 (d, 2H, J=7.5 Hz), 7.02-7.12 (m, 3H), 7.21-7.28 (m, 4H), 8.39 (br s, 1H). 13C NMR (CDCl3) δ 13.81, 19.54, 29.32, 30.67, 31.31, 40.24, 43.98, 48.67, 52.54, 56.18, 60.96, 112.31, 124.37, 124.68, 126.63, 127.30, 127.77, 128.88, 129.70, 130.16, 134.41, 134.83, 138.96, 142.53, 149.98, 170.32, 172.18. ES-MS m/z 575 (M+H). Anal. Calcd. for C34H43N4ClO2.0.5CH2Cl2: C, 67.09; H, 7.18; N, 9.07. Found. C, 66.75; H, 7.12; N, 8.94.

Sources & evidence

ORD record
ord-11b9caf25f16407da6af7823a4086b4a
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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