Cyclopropanecarbonyl chloride → HCID 178488341, compound

HRID 1695595Notes

Reaction equation

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

Participants

Reactant 2

HCID 77637Cyclopropanecarbonyl chloride

HCID 178488336HCID 178488336, compound

Product 1

HCID 178488341HCID 178488341, compoundYield 97.1%

Procedure

Prepared from rac-N2-(8-methoxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-4H-benzo[d][1,3]oxazine-2,6-diamine (Example 22) (162 mg, 0.50 mmol, HPLC 1.090 min) and cyclopropanecarbonyl chloride (53 ul, 0.55 mmol) according to the procedure described for Example 17. Obtained the title compound as an off-white solid (190 mg, 90%, HPLC 1.479 min 93%), MS (ISP) m/e=392.2 [(M+H)+].

Sources & evidence

ORD record: ord-91e2dcfc71a04439b0e492342aeab453
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163740B2

Reaction notes

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