Triethylamine → HCID 54041039, compound

HRID 488426Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:37][CH2:38][CH:39]4[CH2:41][CH2:40]4)=[C:17]([NH:20][C:21](=[O:36])[CH:22]=[CH:23][CH2:24][N:25]4[CH2:30][CH2:29][NH:28][CH2:27][CH:26]4[C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8].C(N(CC)CC)C.[CH3:49][S:50](Cl)(=[O:52])=[O:51].C(Cl)Cl.CO>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:37][CH2:38][CH:39]4[CH2:40][CH2:41]4)=[C:17]([NH:20][C:21](=[O:36])[CH:22]=[CH:23][CH2:24][N:25]4[CH2:30][CH2:29][N:28]([S:50]([CH3:49])(=[O:52])=[O:51])[CH2:27][CH:26]4[C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

Conditions

Temperature: 0 °C

Procedure

A stirred mixture of 500 mg 4-[(3-chloro-4-fluoro-phenyl)-amino]-6-({4-[2-(ethoxycarbonyl)-piperazin-1-yl]-1-oxo-2-buten-1-yl}amino)-7-cyclopropylmethoxy-quinazoline and 0.20 ml triethylamine in 5 ml of methylene chloride is cooled in an ice/water bath, and 80 μl of methanesulfonyl chloride are added dropwise. The reaction mixture is stirred for one hour at 0° C. and another two hours at room temperature. Aqueous work-up followed by column chromatography on silica gel with methylene chloride/methanol (97:2) gives the title compound as a slightly yellow solid. Yield: 395 mg (70% of theory), Melting point: 170-173° C. Mass spectrum (ESI+): m/z=661, 663 [M+H]+

Workup

temperatureis cooled in an ice/water bath

Sources & evidence

ORD record: ord-e3cbdffb6434437b8db9baa3ad4abcef
Source dataset: uspto-grants-2005_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06972288B1

Reaction notes

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