4-Piperidinecarboxylic acid → 4'-(4-(2-Methoxy-phenylsulfanyl)-3-trifluoromethyl-phenyl)-3,4,5,6-tetrahydro-2H-(1,2')bipyridinyl-4-carboxylic acid

HRID 1246850Notes

Reaction equation

HRID 1246850 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[CH2:41][CH2:40][CH:36]([C:37]([OH:39])=[O:38])[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[CH2:41][CH2:40][CH:36]([C:37]([OH:39])=[O:38])[CH2:35][CH2:34]3)[CH:7]=2)=[CH:9][C:10]=1[C:23]([F:26])([F:25])[F:24]

Participants

4

Reactant 3

HCID 37734-Piperidinecarboxylic acidHCID 982104-HydroxypyrrolidineHCID 219068092-Chloro-4-(4-(2-methoxy-phenylsulfanyl)-3-trifluoromethyl-phenyl)-pyridine

Product 1

HCID 219067644'-(4-(2-Methoxy-phenylsulfanyl)-3-trifluoromethyl-phenyl)-3,4,5,6-tetrahydro-2H-(1,2')bipyridinyl-4-carboxylic acid

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 isonipecotic acid. A yellow solid 106 was obtained (0.0225 g, 47%). 1H-NMR (CDCl3, 400 MHz) δ 1.90–1.99 (m, 2H), 2.09–2.16 (m, 2H), 2.68–2.77 (m, 1H), 3.43–3.50 (m, 2H), 3.83 (s, 3H), 4.14–4.20 (m, 2H), 6.95 (d, J=6.2 Hz, 1H), 6.99–7.05 (m, 3H), 7.06 (d, J=8.4 Hz, 1H), 7.45–7.52 (m, 3H), 7.84 (s, 1H), 8.20 (d, J=6.6 Hz, 1H); MS (APCI) m/z 489 (M+H)+.

Sources & evidence

ORD record
ord-1a96a44f052e4a39aeb7b58021d70732
Source dataset
uspto-grants-2006_10
Patent number
US07129247B2

Reaction notes

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