Chloroacetyl chloride → HCID 178488343, compound

HRID 1695584Notes

Reaction equation

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

Participants

Reactant 2

HCID 6577Chloroacetyl chloride

HCID 178488337HCID 178488337, compound

Product 1

HCID 178488343HCID 178488343, compoundYield 95.1%

Procedure

Prepared from rac-N2-(4-methoxy-2,3-dihydro-benzofuran-3-yl)-4H-benzo[d][1,3]oxazine-2,6-diamine (Example 6) (320 mg, 1.03 mmol) and chloroacetyl chloride (85.8 ul, 1.08 mmol) according to the procedure described for Example 3 step A. Obtained the title compound as an off-white solid (380 mg, 95%), MS (ISP) m/e=388.2 [(M+H)+] and 390 [(M+2+H)+].

Sources & evidence

ORD record: ord-7ea917288c3e441587610627358b995d
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163740B2

Reaction notes

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