4-Hydroxypyrrolidine → HCID 21906803, compound

HRID 1005808Notes

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.[NH:33]1[CH2:38][CH2:37][CH:36]([CH2:39][OH:40])[CH2:35][CH2:34]1>>[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:33]3[CH2:38][CH2:37][CH:36]([CH2:39][OH:40])[CH2:35][CH2:34]3)[CH:7]=2)=[CH:9][C:10]=1[C:23]([F:26])([F:25])[F:24]

Participants

Reactant 3

HCID 982104-Hydroxypyrrolidine

HCID 4207714-Piperidinemethanol

HCID 219068092-Chloro-4-(4-(2-methoxy-phenylsulfanyl)-3-trifluoromethyl-phenyl)-pyridine

Product 1

HCID 21906803HCID 21906803, 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 4-piperidinemethanol. A yellow solid 101 was obtained (0.0299 g, 64%). 1H-NMR (CDCl3, 400 MHz) δ 1.41-1.50 (m, 2H), 1.86-1.94 (m, 1H), 1.97-2.03 (m, 2H), 3.27 (t, J=13.6 Hz, 2H), 3.57 (d, J=5.8 Hz, 2H), 3.83 (s, 3H), 4.38 (d, J=13.5 Hz, 2H), 6.93 (d, J=6.6 Hz, 1H), 6.97 (s, 1H), 7.01-7.07 (m, 3H), 7.46-7.52 (m, 3H), 7.84 (s, 1H), 8.24 (d, J=6.2 Hz, 1H); MS (APCI) m/z 475 (M+H)+.

Sources & evidence

ORD record: ord-dd9db95895df4a16a0c1a24efa6754f1
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06787542B2

Reaction notes

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