2,2-Diphenylacetyl chloride → N-[6-(1-{3-[(diphenylacetyl)amino]propyl}-4-piperidinyl)-2-pyridinyl]-2-methylpropanamide

HRID 1269184Notes

Reaction equation

HRID 1269184 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[N:32]=[C:31]([NH:33][C:34](=[O:38])[CH:35]([CH3:37])[CH3:36])[CH:30]=[CH:29][CH:28]=2)[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[CH2:22][CH2:23][CH:24]([C:27]3[N:32]=[C:31]([NH:33][C:34](=[O:38])[CH:35]([CH3:36])[CH3:37])[CH:30]=[CH:29][CH:28]=3)[CH2:25][CH2:26]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 746372,2-Diphenylacetyl chlorideHCID 21957182N-{6-[1-(3-aminopropyl)-4-piperidinyl]-2-pyridinyl}2-methylpropanamide

Product 1

HCID 21957253N-[6-(1-{3-[(diphenylacetyl)amino]propyl}-4-piperidinyl)-2-pyridinyl]-2-methylpropanamide

Procedure

Example 6 was prepared from diphenylacetyl chloride and N-{6-[1-(3-aminopropyl)-4-piperidinyl]-2-pyridinyl}-2-methylpropanamide according to the procedures described in Scheme 8: 1H NMR (400 MHz, CDCl3) δ 8.07 (d, 1H, J=8.0 Hz), 7.71–7.63 (m, 3H), 7.42–7.23 (m, 10H), 6.89 (d, 1H, J=7.6 Hz), 4.96 (s, 1H), 3.41 (dd, 2H, J=5.6, 7.6 Hz), 3.00 (d, 2H, J=11.6 Hz), 2.60 (m, 1H), 2.47 (t, 2H, J=6.4 Hz), 2.45 (m, 1H), 2.06–2.01 (m, 2H), 1.89–1.64 (m, 6H), 1.13 (d, 6H, J=6.8 Hz); ESMS m/e: 499.3 (M+H)+.

Sources & evidence

ORD record
ord-86fcf8daa83243c8b27c243626ac59cb
Source dataset
uspto-grants-2007_04
Patent number
US07199135B2

Reaction notes

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