Pyridine → HCID 178473340, compound

HRID 507041Notes

Reaction equation

HRID 507041 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].N1C=CC=CC=1.[F:13][C:14]([F:49])([F:48])[C:15]1[CH:16]=[C:17]([CH:41]=[C:42]([C:44]([F:47])([F:46])[F:45])[CH:43]=1)[CH2:18][N:19]([CH:25]1[CH2:31][CH2:30][CH2:29][NH:28][C:27]2[CH:32]=[C:33]([C:37]([F:40])([F:39])[F:38])[C:34]([CH3:36])=[CH:35][C:26]1=2)[C:20]1[NH:24][N:23]=[N:22][N:21]=1>ClCCl>[CH2:5]([O:4][C:2]([N:28]1[CH2:29][CH2:30][CH2:31][CH:25]([N:19]([CH2:18][C:17]2[CH:41]=[C:42]([C:44]([F:47])([F:46])[F:45])[CH:43]=[C:15]([C:14]([F:13])([F:49])[F:48])[CH:16]=2)[C:20]2[NH:24][N:23]=[N:22][N:21]=2)[C:26]2[CH:35]=[C:34]([CH3:36])[C:33]([C:37]([F:39])([F:38])[F:40])=[CH:32][C:27]1=2)=[O:3])[CH3:6]

Participants

5

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 178421834HCID 178421834, compound

Product 1

HCID 178473340HCID 178473340, compoundYield 20.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add ethyl chloroformate (0.24 mmol) and pyridine (0.24 mmol) to a dichloromethane (5 mL) solution of (3,5-bis-trifluoromethyl-benzyl)-(7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-(1H-tetrazol-5-yl)-amine (0.045 g, 0.08 mmol). After stirring 14 h, wash the reaction with 5% HCl (3 mL), water (3 mL) and brine (3 mL). Dry the organic portion over sodium sulfate and filter. Chromatograph the crude product, eluting with ethyl acetate/hexane (20-60%), to provide the title compound (0.01 g, 20%) as an oil: MS (ES+): 611 (M+H).

Workup

  1. washwash
  2. customthe reaction with 5% HCl (3 mL), water (3 mL) and brine (3 mL)
  3. dry with materialDry the organic portion over sodium sulfate
  4. filtrationfilter
  5. washChromatograph the crude product, eluting with ethyl acetate/hexane (20-60%)

Sources & evidence

ORD record
ord-e0f019eca3fa45ffae92e8a8028cf955
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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