Formaldehyde → HCID 57979801, compound

HRID 1867730Notes

Reaction equation

HRID 1867730 reaction equation
[Cl:1][C:2]1[C:3]([F:23])=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([CH:19]=O)[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.[NH2:24][CH:25]([CH:29]1[CH2:33][CH2:32][N:31]([C:34](OC(C)(C)C)=O)[CH2:30]1)[C:26]([OH:28])=[O:27].[CH2:41]=O>>[Cl:1][C:2]1[C:3]([F:23])=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([CH2:19][N:24]([CH:25]([CH:29]4[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30]4)[C:26]([OH:28])=[O:27])[CH3:41])[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 712FormaldehydeHCID 115734924-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazoline-6-carbaldehydeHCID 22309149α-Amino-1-[(1,1-dimethylethoxy)carbonyl]-3-pyrrolidineacetic acid

Product 1

HCID 57979801HCID 57979801, compound

Procedure

4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazoline-6-carbaldehyde was coupled with amino[1-(tert-butoxycarbonyl)pyrrolidin-3-yl]acetic acid, deprotected and methylated by reaction with aqueous formaldehyde using analogous methods to those described for the equivalent steps in Example 68 to give [({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(methyl)amino](1-methylpyrrolidin-3-yl)acetic acid as a pale yellow foam; Mass Spectrum: (M+H)+ 488.

Sources & evidence

ORD record
ord-263fa2ca6d7c40769dcdf73ae582e758
Source dataset
uspto-grants-2009_12
Patent number
US07632840B2

Reaction notes

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