4-Piperidinecarboxamide → HCID 60108841, compound

HRID 1005828Notes

Reaction equation

HRID 1005828 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([S:11][C:12]3[CH:17]=[CH:16][C:15]([C:18]4[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=4)=[CH:14][C:13]=3[C:24]([F:27])([F:26])[F:25])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.OC1CCNC1.[NH:34]1[CH2:42][CH2:41][CH:37]([C:38]([NH2:40])=[O:39])[CH2:36][CH2:35]1>>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([S:11][C:12]3[CH:17]=[CH:16][C:15]([C:18]4[CH:19]=[CH:20][N:21]=[C:22]([N:34]5[CH2:42][CH2:41][CH:37]([C:38]([NH2:40])=[O:39])[CH2:36][CH2:35]5)[CH:23]=4)=[CH:14][C:13]=3[C:24]([F:25])([F:26])[F:27])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 37724-PiperidinecarboxamideHCID 982104-HydroxypyrrolidineHCID 865858674-(4-(2,3-Dihydro-benzo(1,4)dioxin-6-ylsulfanyl)-3-trifluoromethyl-phenyl)-pyridine

Product 1

HCID 60108841HCID 60108841, compound

Procedure

The title compound was prepared according to the procedures of Example 38E, substituting compound 76 with compound 118 (0.033 g, 0.0779 mmol) and 3-hydroxypyrrolidine with isonipecotamide. A yellow solid 126 was obtained (0.024 g, 47%). 1H-NMR (CDCl3, 400 MHz) δ 1.90-1.99 (m, 2H), 2.08-2.14 (m, 2H), 2.58-2.65 (m, 1H), 3.38-3.45 (m, 2H), 4.28-4.34 (m, 6H), 5.55 (br s, 1H), 5.97 (br s, 1H), 6.93-6.98 (m, 3H), 7.05 (dd, J=2.0 Hz, 8.2 Hz, 1H), 7.09 (d, J=1.8 Hz, 1H), 7.12 (d, J=8.4 Hz, 1H), 7.53 (d, J=8.4 Hz, 1H), 7.82 (s, 1H), 8.21 (d, J=6.6 Hz, 1H); MS (APCI) m/z 516 (M+H)+.

Sources & evidence

ORD record
ord-7118196f5b0e4db09709c711884f6467
Source dataset
uspto-grants-2004_09
Patent number
US06787542B2

Reaction notes

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