Phosgene → 7-[6-(1H-imidazol-2-yl)pyridin-3-yl]-2,3-dihydro-1,4-benzoxazepin-4(5H)-carbonyl chloride

HRID 473913Notes

Reaction equation

HRID 473913 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[N:11]=[CH:10][C:9]([C:12]2[CH:13]=[CH:14][C:15]3[O:21][CH2:20][CH2:19][NH:18][CH2:17][C:16]=3[CH:22]=2)=[CH:8][CH:7]=1.C(N(C(C)C)CC)(C)C.[C:32](Cl)([Cl:34])=[O:33]>ClCCl.C1(C)C=CC=CC=1>[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[N:11]=[CH:10][C:9]([C:12]2[CH:13]=[CH:14][C:15]3[O:21][CH2:20][CH2:19][N:18]([C:32]([Cl:34])=[O:33])[CH2:17][C:16]=3[CH:22]=2)=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 6371PhosgeneHCID 81531DiisopropylethylamineHCID 675137447-[6-(1H-imidazol-2-yl)pyridin-3-yl]-2,3,4,5-tetrahydro-1,4-benzoxazepine

Product 1

HCID 866720357-[6-(1H-imidazol-2-yl)pyridin-3-yl]-2,3-dihydro-1,4-benzoxazepin-4(5H)-carbonyl chloride

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

The 7-[6-(1H-imidazol-2-yl)pyridin-3-yl]-2,3,4,5-tetrahydro-1,4-benzoxazepine as obtained in step 3 was dissolved in dichloromethane (2 mL), diisopropylethylamine (0.12 mL, 0.65 mmol) was added, followed by addition of phosgene (0.07 mL of a 20% solution in toluene, 0.13 mmol). The reaction mixture was stirred at room temperature for 30 min and then concentrated to afford crude 7-[6-(1H-imidazol-2-yl)pyridin-3-yl]-2,3-dihydro-1,4-benzoxazepin-4(5H)-carbonyl chloride.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-7e4ea96e92de410da31d1c2176baa87c
Source dataset
uspto-grants-2014_01
Patent number
US08637499B2

Reaction notes

Loading…