Piperidine → t-Butyl[2-({4-[3-cyano-5-(piperidin-1-ylmethyl)pyridin-2-yl]benzoyl}amino)phenyl]carbamate

HRID 599519Notes

Reaction equation

HRID 599519 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:33])[C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:28]([C:29]#[N:30])=[CH:27][C:26]([CH:31]=O)=[CH:25][N:24]=2)=[CH:19][CH:18]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1>ClCCl>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:33])[C:17]1[CH:18]=[CH:19][C:20]([C:23]2[C:28]([C:29]#[N:30])=[CH:27][C:26]([CH2:31][N:34]3[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]3)=[CH:25][N:24]=2)=[CH:21][CH:22]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 86624985HCID 86624985, compound

Product 1

HCID 59848782t-Butyl[2-({4-[3-cyano-5-(piperidin-1-ylmethyl)pyridin-2-yl]benzoyl}amino)phenyl]carbamateYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of N-(2-t-butoxycarbonylaminophenyl)-4-(3-cyano-5-formylpyridin-2-yl)benzamide (400 mg, 0.905 mmol, prepared as described in Method 15) in dichloromethane (5 ml) was added over 20 min to a stirred mixture of piperidine (0.1 ml, 1.00 mmol) sodium triacetoxyborohydride (212 mg, 1.0 mmol), powdered 3A molecular sieve (500 mg) and dichloromethane (15 ml) at −20° C. under nitrogen. The reaction mixture was stirred for 16 hours at ambient temperature before being filtered and washed with saturated aqueous sodium hydrogen carbonate, dried over sodium sulfate and evaporated. The crude product was purified by chromatography on silica eluting with ethyl acetate to afford the title compound as a cream solid (252 mg, 55%); NMR Spectrum: (DMSO-d6) 1.40 (m, 2H), 1.45 (s, 9H), 1.46 (m, 4H), 2.39 (m 4H), 3.58 (s, 2H), 7.17 (m, 2H), 7.56 (m, 2H), 8.01 (d, 2H), 8.12 (d, 2H), 8.31 (d, 1H), 8.69 (s, 1H), 8.87 (d, 1H), 9.94 (s, 1H); Mass Spectrum: M+H+512.

Workup

  1. customat −20° C.
  2. filtrationbefore being filtered
  3. washwashed with saturated aqueous sodium hydrogen carbonate
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customThe crude product was purified by chromatography on silica eluting with ethyl acetate

Sources & evidence

ORD record
ord-07d9dc8d8e0946d389eb0fb2f0fda0a1
Source dataset
uspto-grants-2011_03
Patent number
US07897778B2

Reaction notes

Loading…