Formaldehyde → HCID 57979806, compound

HRID 1867729Notes

Reaction equation

HRID 1867729 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][C:25]1([C:37]([OH:39])=[O:38])[CH2:29][CH2:28][N:27]([C:30](OC(C)(C)C)=O)[CH2:26]1.N[C:41]1(C(O)=O)CCN(C(OC(C)(C)C)=O)CC1.C=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]([CH3:41])[C:25]4([C:37]([OH:39])=[O:38])[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26]4)[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 6937974-Amino-1-(tert-butoxycarbonyl)piperidine-4-carboxylic acidHCID 115734924-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazoline-6-carbaldehydeHCID 247303163-Amino-1-(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid

Product 1

HCID 57979806HCID 57979806, compound

Procedure

4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazoline-6-carbaldehyde was coupled with 3-amino-1-(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid (commercially available or may be prepared made using analogous methodology as that described for the preparation of 4-amino-1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid in J. Org. Chem. 1996, 61, 7650-7651). The resultant product was deprotected and methylated by reaction with aqueous formaldehyde using analogous methods to those described for the equivalent steps in Example 68 to give 3-[({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(methyl)amino]-1-methylpyrrolidine-3-carboxylic acid as a pale yellow foam; Mass Spectrum: (M+H)+ 474.

Workup

  1. custommay be prepared

Sources & evidence

ORD record
ord-a7144fa7b28c43c0b027b76b5adb3f43
Source dataset
uspto-grants-2009_12
Patent number
US07632840B2

Reaction notes

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