Cyclopropanesulfonyl chloride → 2-(1-(Cyclopropylsulfonyl)piperidin-4-yloxy)-6-(1-(propylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl)benzo[d]thiazole

HRID 1429542Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][CH:4]([O:7][C:8]2[S:9][C:10]3[CH:16]=[C:15]([C:17]4[CH2:18][CH2:19][N:20]([S:23]([CH2:26][CH2:27][CH3:28])(=[O:25])=[O:24])[CH2:21][CH:22]=4)[CH:14]=[CH:13][C:11]=3[N:12]=2)[CH2:3][CH2:2]1.[CH:29]1([S:32](Cl)(=[O:34])=[O:33])[CH2:31][CH2:30]1>>[CH:29]1([S:32]([N:1]2[CH2:2][CH2:3][CH:4]([O:7][C:8]3[S:9][C:10]4[CH:16]=[C:15]([C:17]5[CH2:18][CH2:19][N:20]([S:23]([CH2:26][CH2:27][CH3:28])(=[O:25])=[O:24])[CH2:21][CH:22]=5)[CH:14]=[CH:13][C:11]=4[N:12]=3)[CH2:5][CH2:6]2)(=[O:34])=[O:33])[CH2:31][CH2:30]1

Participants

Reactant 2

HCID 2760919Cyclopropanesulfonyl chloride

HCID 67468519HCID 67468519, compound

Product 1

HCID 545965252-(1-(Cyclopropylsulfonyl)piperidin-4-yloxy)-6-(1-(propylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl)benzo[d]thiazole

Procedure

Example 22 was prepared from Compound 15A and cyclopropanesulfonyl chloride in a similar manner to the procedure described for Example 1. 1H NMR (599 MHz, DMSO-d6) δ ppm 7.93 (s, 1H), 7.62 (d, J=8.2 Hz, 1H), 7.50 (d, J=8.8 Hz, 1H), 6.23 (br. s., 1H), 5.35 (ddd, J=7.5, 3.7, 3.5 Hz, 1H), 3.96 (br. s., 2H), 3.50 (t, J=5.6 Hz, 4H), 3.35 (m, 2H), 3.00-3.14 (m, 2H), 2.60-2.69 (m, 3H), 2.15-2.26 (m, 2H), 1.98 (d, J=7.6 Hz, 2H), 1.70-1.82 (m, 2H), 0.94-1.10 (m, 7H). LC/MS (m/z)=526 (M+H)+.

Sources & evidence

ORD record: ord-255f8ad8dc2c440db3bd76f9b41f056b
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940716B2

Reaction notes

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