Borane;tetrahydrofuran → 1-Methylethyl 4-[({6-[2-fluoro-4-(methylthio)phenyl]-3-pyridinyl}amino)methyl]-1-piperidinecarboxylate

HRID 423684Notes

Reaction equation

HRID 423684 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([S:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]1[N:15]=[CH:14][C:13]([NH:16][C:17]([CH:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][CH:28]([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]2)=O)=[CH:12][CH:11]=1.B.C1COCC1>C1COCC1>[F:1][C:2]1[CH:7]=[C:6]([S:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]1[N:15]=[CH:14][C:13]([NH:16][CH2:17][CH:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][CH:28]([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]2)=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuran2×HCID 666732541-Methylethyl 4-[({6-[2-fluoro-4-(methylthio)phenyl]-3-pyridinyl}amino)carbonyl]-1-piperidinecarboxylate

Product 1

HCID 666731911-Methylethyl 4-[({6-[2-fluoro-4-(methylthio)phenyl]-3-pyridinyl}amino)methyl]-1-piperidinecarboxylateYield 49.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Methylethyl 4-[({6-[2-fluoro-4-(methylthio)phenyl]-3-pyridinyl}amino)methyl]-1-piperidinecarboxylate (195 mg, 49%) was prepared as a yellow solid from 1-methylethyl 4-[({6-[2-fluoro-4-(methylthio)phenyl]-3-pyridinyl}amino)carbonyl]-1-piperidinecarboxylate (410 mg, 0.95 mmol), 1M BH3-THF (2.85 mL, 2.85 mmol) and THF (5 mL) in a manner similar to Example 172, Step 3, except that no 1.8M BH3-THF was used. 1H NMR (400 MHz, CDCl3): δ 8.45 (bs, 1H), 7.70 (d, 1H, J=9.0 Hz), 7.64-7.56 (m, 1H), 7.35 (d, 1H, J=9.1 Hz), 7.11 (d, 1H, J=8.2 Hz), 7.01 (d, 1H, J=11.8 Hz), 4.95-4.82 (m, 1H), 4.24-4.08 (m, 2H), 3.08 (d, 2H, J=5.1 Hz), 2.80-2.60 (m, 2H), 2.50 (d, 3H, J=2.1 Hz), 1.85-1.70 (m, 2H), 1.32-1.09 (m, 8H); LRMS (ESI), m/z 418 (M+H).

Sources & evidence

ORD record
ord-4a6aaf12e54c4cb8ac745a269272be0e
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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