Trifluoroacetic acid → HCID 69372777, compound

HRID 1168693Notes

Reaction equation

HRID 1168693 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:45][CH2:46][CH:47]4[CH2:49][CH2:48]4)=[C:17]([NH:20][C:21](=[O:44])[CH:22]=[CH:23][CH2:24][N:25]4[CH2:30][CH2:29][CH:28]([N:31]([CH2:36][C:37]([O:39][C:40]([CH3:43])(C)C)=[O:38])[CH2:32][C@H](O)C)[CH2:27][CH2:26]4)[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8].C(Cl)Cl.CO.FC(F)(F)C(O)=O.C(OCC)(=O)C.CO>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:45][CH2:46][CH:47]4[CH2:49][CH2:48]4)=[C:17]([NH:20][C:21](=[O:44])[CH:22]=[CH:23][CH2:24][N:25]4[CH2:26][CH2:27][CH:28]([N:31]5[CH2:32][C@@H:40]([CH3:43])[O:39][C:37](=[O:38])[CH2:36]5)[CH2:29][CH2:30]4)[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 21226129Dichloromethane methanolHCID 21584119Ethylacetate methanolHCID 69373553HCID 69373553, compound

Product 1

HCID 69372777HCID 69372777, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Prepared by lactonizing the intermediate product ((R)-4-[(3-chloro-4-fluorophenyl)amino]-6 ({4-[4-[N-(tert-butyloxycarbonylmethyl)-N-(2-hydroxypropyl)amino]piperidin-1-y]-1-oxo-2-buten-1-yl}amino)-7-cyclopropylmethoxyquinazoline, melting point: from 115° C. (with foaming); Rf value: 0.53 (silica gel, methylene chloride/methanol 9:1)) in the presence of 5 equivalents of trifluoroacetic acid in acetonitrile under reflux; melting point: from 126° C. (with foaming); mass spectrum (ESI+): m/z=623, 625 [M+H]+; Rf value: 0.29 (silica gel, ethyl acetate/methanol 4:1).

Workup

  1. customPrepared
  2. temperatureunder reflux
  3. customfrom 126° C.

Sources & evidence

ORD record
ord-271a6d69be9b4dc190aee9dc8237c6db
Source dataset
uspto-grants-2003_09
Patent number
US06627634B2

Reaction notes

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