2,2-Diphenylacetyl chloride → N-[3-(1-{3-[(diphenylacetyl)amino]propyl}-4-piperidinyl)-4-fluorophenyl]-2-methylpropanamide

HRID 1269202Notes

Reaction equation

HRID 1269202 reaction equation
[C:1]1([CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:17][CH2:18][CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][CH:24]([C:27]2[CH:28]=[C:29]([NH:34][C:35](=[O:39])[CH:36]([CH3:38])[CH3:37])[CH:30]=[CH:31][C:32]=2[F:33])[CH2:23][CH2:22]1>>[C:1]1([CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([NH:17][CH2:18][CH2:19][CH2:20][N:21]2[CH2:26][CH2:25][CH:24]([C:27]3[CH:28]=[C:29]([NH:34][C:35](=[O:39])[CH:36]([CH3:37])[CH3:38])[CH:30]=[CH:31][C:32]=3[F:33])[CH2:23][CH2:22]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 746372,2-Diphenylacetyl chlorideHCID 21957238N-{3-[1-(3-aminopropyl)-4-piperidinyl]4-fluorophenyl}-2-methylpropanamide

Product 1

HCID 21957211N-[3-(1-{3-[(diphenylacetyl)amino]propyl}-4-piperidinyl)-4-fluorophenyl]-2-methylpropanamide

Procedure

Example 24 was prepared from diphenylacetyl chloride and N-{3-[1-(3-aminopropyl)-4-piperidinyl]-4-fluorophenyl}-2-methylpropanamide according to the procedures described in Scheme 8: 1H NMR (400 MHz, CDCl3) δ 7.95 (s, 1H), 7.47 (dd, 1H, J=2.4, 6.4 Hz), 7.34–7.21 (m, 11H), 7.06 (t, 1H, J=4.8 Hz), 6.91 (t, 1H, J=10.0 Hz), 4.90 (s, 1H), 3.38 (dd, 2H, J=6.0, 11.6 Hz), 2.90–2.87 (m, 2H), 2.74 (m, 1H), 2.50 (m, 1H), 2.36 (t, 2H, J=6.8 Hz), 1.96 (dt, 2H, J=2.8, 12.0 Hz), 1.73–1.62 (m, 6H), 1.20 (d, 6H, J=6.8 Hz); ESMS m/e: 516.3 (M+H)+.

Sources & evidence

ORD record
ord-60196de8e409415cbb8310fd38edbd5b
Source dataset
uspto-grants-2007_04
Patent number
US07199135B2

Reaction notes

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