Cyclopropanecarbonyl chloride → HCID 178521736, compound

HRID 1695647Notes

Reaction equation

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

Participants

Reactant 2

HCID 77637Cyclopropanecarbonyl chloride

HCID 178507252HCID 178507252, compound

Product 1

HCID 178521736HCID 178521736, compoundYield 50%

Procedure

Prepared from rac-N2-chroman-4-yl-4H-benzo[d][1,3]oxazine-2,6-diamine (Example 75) (295 mg, 1.0 mmol, HPLC 0.699 min) and cyclopropanecarbonyl chloride (115 mg, 0.55 mmol) according to the procedure described for Example 27. Obtained the title compound as an off-white foam (100 mg, 28%, HPLC 1.353 min), MS (ISP) m/e=364.3 [(M+H)+].

Sources & evidence

ORD record: ord-2907ef8b7fcf4b2dbf1486dad6884ac3
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163740B2

Reaction notes

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