Cyclopropanesulfonyl chloride → HCID 178488354, compound

HRID 1695657Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[CH:10]([NH:12][C:13]1[O:14][CH2:15][C:16]3[CH:22]=[C:21]([NH2:23])[CH:20]=[CH:19][C:17]=3[N:18]=1)[CH2:9][CH2:8]2.[CH:24]1([S:27](Cl)(=[O:29])=[O:28])[CH2:26][CH2:25]1>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[CH:10]([NH:12][C:13]1[O:14][CH2:15][C:16]3[CH:22]=[C:21]([NH:23][S:27]([CH:24]4[CH2:26][CH2:25]4)(=[O:29])=[O:28])[CH:20]=[CH:19][C:17]=3[N:18]=1)[CH2:9][CH2:8]2

Participants

Reactant 2

HCID 2760919Cyclopropanesulfonyl chloride

HCID 178488335HCID 178488335, compound

Product 1

HCID 178488354HCID 178488354, compoundYield 61.4%

Procedure

Prepared from rac-N2-(7-methoxy-indan-1-yl)-4H-benzo[d][1,3]oxazine-2,6-diamine (Example 10) (155 mg, 0.50 mmol, HPLC 0.776 min) and cyclopropanesulfonyl chloride (77 mg, 0.55 mmol) according to the procedure described for Example 27. Obtained the title compound as a light brown solid (127 mg, 61%, HPLC 1.366 min), MS (ISP) m/e=414.2 [(M+H)+].

Sources & evidence

ORD record: ord-adba93f06cad4e18a77a884dac65bb7b
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163740B2

Reaction notes

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