Chloroacetyl chloride → HCID 178520798, compound

HRID 1695611Notes

Reaction equation

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

Participants

Reactant 2

HCID 6577Chloroacetyl chloride

HCID 178507253HCID 178507253, compound

Product 1

HCID 178520798HCID 178520798, compoundYield 27%

Procedure

Prepared from rac-N2-(6-fluoro-2,3-dihydro-benzofuran-3-yl)-4H-benzo[d][1,3]oxazine-2,6-diamine (Example 34) (748 mg, 2.5 mmol, HPLC 0.641 min) and chloroacetyl chloride (0.21 ml, 2.625 mmol) according to the procedure described for Example 3 step A. Obtained the title compound as a white solid (250 mg, 27%, HPLC 1.056 min), MS (ISP) m/e=376.1 [(M+H)+] and 378 [(M+2+H)+].

Sources & evidence

ORD record: ord-80b9f1b37d7a4336a218aaffa3e90781
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163740B2

Reaction notes

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