2,2-Diphenylacetyl chloride → N-[5-(1-{3-[(diphenylacetyl)amino]propyl}-4-piperidinyl)-2-fluorophenyl]butanamide

HRID 1269243Notes

Reaction equation

HRID 1269243 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]=[CH:29][C:30]([F:39])=[C:31]([NH:33][C:34](=[O:38])[CH2:35][CH2:36][CH3:37])[CH:32]=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[CH:28]=[CH:29][C:30]([F:39])=[C:31]([NH:33][C:34](=[O:38])[CH2:35][CH2:36][CH3:37])[CH:32]=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 21957132N-{5-[1-(3-aminopropyl)4-piperidinyl]-2-fluorophenyl}butanamide

Product 1

HCID 21957146N-[5-(1-{3-[(diphenylacetyl)amino]propyl}-4-piperidinyl)-2-fluorophenyl]butanamide

Procedure

Example 65 was prepared from diphenylacetyl chloride and N-{5-[1-(3-aminopropyl)-4-piperidinyl]-2-fluorophenyl}butanamide according to the procedures described in Scheme 8: 1H NMR (400 MHz, CDCl3) δ 8.33–8.18 (m, 1H), 7.49–7.10 (m, 12H), 7.10–6.93 (m, 1H), 6.90–6.76 (br, 1H), 4.87 (s, 1H), 3.44–3.28 (m, 2H), 3.06–2.89 (m, 2H), 2.56–2.40 (m, 3H), 2.40–2.31 (m, 2H), 2.13–1.93 (m, 2H), 1.86–1.52 (m, 8H), 1.01 (t, 3H, J=7.6 Hz); ESMS m/e: 516.6 (M+H)+; Anal. Calc. For (HCl salt) C32H39ClFN3O2.0.25CHCl3.1.00H2O: C, 64.49; H, 6.93; N, 6.99. Found: C, 64.23; H, 7.21; N, 6.99.

Sources & evidence

ORD record
ord-e1d76fbaa8c84dba8dc29bdeba65e6dc
Source dataset
uspto-grants-2007_04
Patent number
US07199135B2

Reaction notes

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