2-Chlorobenzenesulfonyl chloride → 2-Chloro-N-[(6R,7aS)-3-oxo-2-(4-trifluoromethoxy-phenyl)-hexahydro-pyrrolo[1,2-c]imidazol-6-yl]-benzenesulfonamide

HRID 455259Notes

Reaction equation

HRID 455259 reaction equation
[NH2:1][C@H:2]1[CH2:21][N:5]2[C:6](=[O:20])[N:7]([C:9]3[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=3)[CH2:8][C@@H:4]2[CH2:3]1.[Cl:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[S:29](Cl)(=[O:31])=[O:30]>>[Cl:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[S:29]([NH:1][C@H:2]1[CH2:21][N:5]2[C:6](=[O:20])[N:7]([C:9]3[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:17])[F:18])=[CH:11][CH:10]=3)[CH2:8][C@@H:4]2[CH2:3]1)(=[O:31])=[O:30]

Participants

3

Reactant 2

HCID 761872-Chlorobenzenesulfonyl chlorideHCID 70976166(6R,7aS)-6-Amino-2-(4-trifluoromethoxy-phenyl)-hexahydro-pyrrolo[1,2-c]imidazol-3-one

Product 1

HCID 709762742-Chloro-N-[(6R,7aS)-3-oxo-2-(4-trifluoromethoxy-phenyl)-hexahydro-pyrrolo[1,2-c]imidazol-6-yl]-benzenesulfonamideYield 27%

Procedure

In analogy to the procedure described for the synthesis of 2-Chloro-N-[(6R,7aS)-3-oxo-2-(4-trifluoromethoxy-phenyl)-hexahydro-pyrrolo[1,2-c]imidazol-6-yl]-benzamide (example 1, step i) the title compound was prepared from (6R,7aS)-6-Amino-2-(4-trifluoromethoxy-phenyl)-hexahydro-pyrrolo[1,2-c]imidazol-3-one (example 1, step h) and 2-chlorobenzene-1-sulfonyl chloride to yield 27% the title compound. 1H NMR (300 MHz, CDCl3): δ 8.13 (d, 1H, J=7.2 Hz), 7.58-7.45 (m, 6H), 7.19 (d, 2H, J=9.0 Hz), 5.33 (d, 1H, J=6.3 Hz), 4.06-3.98 (m, 3H), 3.94-3.85 (m, 1H), 3.66 (d, 1H, J=6.9 Hz), 2.94 (dd, 1H, J1=12.9 Hz, J2=3.6 Hz), 2.19-2.12 (m, 1H), 1.74-1.64 (m, 1H); LC-MS: 476.0 [M+1]+.

Sources & evidence

ORD record
ord-e8dc158ab6e64eb197483b6bd5575d63
Source dataset
uspto-grants-2013_07
Patent number
US08497288B2

Reaction notes

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