2-Chlorobenzenesulfonyl chloride → HCID 66892942, compound

HRID 1162029Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([O:11][C@@H:12]2[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][C@H:13]2[F:25])[C:5]2[O:9][CH:8]=[CH:7][C:6]=2[CH:10]=1.[Cl:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[S:33](Cl)(=[O:35])=[O:34]>>[ClH:26].[Cl:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[S:33]([NH:1][C:2]1[CH:3]=[C:4]([O:11][C@@H:12]2[CH2:17][CH2:16][NH:15][CH2:14][C@H:13]2[F:25])[C:5]2[O:9][CH:8]=[CH:7][C:6]=2[CH:10]=1)(=[O:35])=[O:34]

Participants

Reactant 2

HCID 761872-Chlorobenzenesulfonyl chloride

HCID 66893726HCID 66893726, compound2×

Product 1

HCID 66892942HCID 66892942, compound

Procedure

The title compound was prepared according to the procedure described for Example 84 starting from tert-butyl trans-4-[(5-amino-1-benzofuran-7-yl)oxy]-3-fluoropiperidine-1-carboxylate (Intermediate 53) and 2-chlorobenzenesulfonyl chloride. Yield: 40 mg (22%), HPLC purity=100%, m/z=425 (M+H)+, 1H NMR (270 MHz, methanol-d4) δ ppm 2.09-2.35 (m, 2H) 3.10-3.57 (m, 3H) 3.62-3.79 (m, 1H) 4.73-4.96 (m, 1H) 4.97-5.23 (m, 1H) 6.74 (d, J=2.23 Hz, 1H) 6.85 (d, J=1.98 Hz, 1H) 7.05 (d, J=1.73 Hz, 1H) 7.31-7.40 (m, 1H) 7.45-7.58 (m, 2H) 7.71 (d, J=2.23 Hz, 1H) 7.96 (dd, J=7.79, 1.61 Hz, 1H).

Sources & evidence

ORD record: ord-2df3e9e4393f41e38144e198c1993d65
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820675B2

Reaction notes

Loading…