Formaldehyde → 1-(Tert-butoxycarbonyl)-4-[({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(methyl)amino]piperidine-4-carboxylic acid

HRID 1867681Notes

Reaction equation

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

Participants

Reactant 2

HCID 712Formaldehyde

HCID 690480781-(Tert-butoxycarbonyl)-4-[({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)amino]piperidine-4-carboxylic acid

Product 1

HCID 690474061-(Tert-butoxycarbonyl)-4-[({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(methyl)amino]piperidine-4-carboxylic acid

Procedure

1-(tert-Butoxycarbonyl)-4-[({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)amino]piperidine-4-carboxylic acid was reacted with paraformaldehyde using an analogous method to that described for the equivalent step in Example 11 to give 1-(tert-butoxycarbonyl)-4-[({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(methyl)amino]piperidine-4-carboxylic acid; 1H NMR Spectrum: (DMSO-d6) 1.39 (s, 9H); 1.80 (m, 2H); 2.00 (m, 2H); 2.26 (s, 3H); 3.18 (m, 2H); 3.62 (m, 2H); 3.73 (s, 2H); 3.94 (s, 3H); 7.20 (s, 1H); 7.29 (t, 1H); 7.50 (t, 1H); 7.56 (t, 1H); 8.30 (s, 1H); 8.43 (s, 1H); 9.73 (s, 1H); 12.70 (brs, 1H). Mass Spectrum: (M+H)+ 574.

Sources & evidence

ORD record: ord-e7201d6f71a44804ae7b8592aeba314c
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07632840B2

Reaction notes

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