1-Piperazinecarboxaldehyde → 4-(4-(4-(2-Methoxy-phenylsulfanyl)-3-trifluoromethyl-phenyl)-pyridin-2-yl)-piperazine-1-carbaldehyde

HRID 1005806Notes

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

Participants

Reactant 3

HCID 821911-Piperazinecarboxaldehyde

HCID 982104-Hydroxypyrrolidine

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

Product 1

HCID 219067554-(4-(4-(2-Methoxy-phenylsulfanyl)-3-trifluoromethyl-phenyl)-pyridin-2-yl)-piperazine-1-carbaldehyde

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 1-formylpiperazine. A yellow solid 99 was obtained (0.0159 g, 34%). 1H-NMR (CDCl3, 400 MHz) δ 3.62-3.65 (m, 2H), 3.68-3.72 (m, 2H), 3.75-3.78 (m, 2H), 3.83 (s, 3H), 3.86-3.89 (m, 2H), 6.95 (s, 1H), 7.02 (m, 3H), 7.08 (d, J=8.4 Hz, 1H), 7.46-7.52 (m, 3H), 7.86 (d, J=1.5 Hz, 1H), 8.16 (s, 1H), 8.30 (d, J=6.2 Hz, 1H), MS (APCI) m/z 474 (M+H)+.

Sources & evidence

ORD record: ord-3fa0d158a086438aaa2589a75c0b65d2
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06787542B2

Reaction notes

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