4-Hydroxypyrrolidine → HCID 21906759, compound

HRID 1005816Notes

Reaction equation

HRID 1005816 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([S:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[O:21][CH3:22])=[C:10]([C:23]([F:26])([F:25])[F:24])[CH:9]=2)[CH:5]=[CH:4][N:3]=1.OC1CCNC1.[C:33]([N:36]1[CH2:42][CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1)(=[O:35])[CH3:34]>>[CH3:22][O:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[S:14][C:11]1[CH:12]=[CH:13][C:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([N:39]3[CH2:40][CH2:41][CH2:42][N:36]([C:33](=[O:35])[CH3:34])[CH2:37][CH2:38]3)[CH:7]=2)=[CH:9][C:10]=1[C:23]([F:26])([F:25])[F:24]

Participants

4

Reactant 3

HCID 982104-HydroxypyrrolidineHCID 4186202N-AcetylhomopiperazineHCID 219068092-Chloro-4-(4-(2-methoxy-phenylsulfanyl)-3-trifluoromethyl-phenyl)-pyridine

Product 1

HCID 21906759HCID 21906759, compound

Procedure

The title compound was prepared according to the procedures of Example 38E, substituting compound 76 with compound 96 (0.039 g, 0.0985 mmol) and 3-hydroxypyrrolidine with N-acetylhomopiperazine. A yellow solid 112 was obtained (0.0246 g, 50%). 1H-NMR (CDCl3, 400 MHz) δ 2.02-2.10 (m, 2H), 2.08 (s, 3H), 3.55 (t, J=5.9 Hz, 1H), 3.59 (t, J=5.5 Hz, 1H), 3.79 (t, J=6.2 Hz, 1H), 3.83 (s, 3H), 3.84-3.92 (m, 3H), 4.05 (t, J=5.3 Hz, 1H), 4.15 (t, J=5.5 Hz, 1H), 6.86 (s, 1/3H), 6.89 (s, 2H), 6.92-7.08 (m, 4H), 7.45-7.53 (m, 3H), 7.84 (s, 1/3H), 7.85 (s, 2/3H), 8.26-8.30 (m, 1H), MS (APCI) m/z 502 (M+H)+.

Sources & evidence

ORD record
ord-c32b2330b8cc4b9ebc65ecf941eca42a
Source dataset
uspto-grants-2004_09
Patent number
US06787542B2

Reaction notes

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