Cyclopropanesulfonyl chloride → Cyclopropanesulfonic acid [2-(3-cyclopropyl-phenylamino)-4H-benzo[d][1,3]oxazin-6-yl]-amide

HRID 1695693Notes

Reaction equation

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

Participants

Reactant 2

HCID 2760919Cyclopropanesulfonyl chloride

HCID 59231769N2-(3-cyclopropyl-phenyl)-4H-benzo[d][1,3]oxazine-2,6-diamine

Product 1

HCID 59231789Cyclopropanesulfonic acid [2-(3-cyclopropyl-phenylamino)-4H-benzo[d][1,3]oxazin-6-yl]-amideYield 9.1%

Procedure

Prepared from N2-(3-Cyclopropyl-phenyl)-4H-benzo[d][1,3]oxazine-2,6-diamine (Example 119) (200 mg, 0.72 mmol) and cyclopropanesulfonyl chloride (161 mg, 1.1 mmol) according to the procedure described for Example 27. Obtained the title compound as an off-white foam (25 mg, 9%), MS (ISP) m/e=382.4 [(M−H)−].

Sources & evidence

ORD record: ord-6cc7af5b3bf948e99fc95ef06d760a0e
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163740B2

Reaction notes

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