Hydrochloric Acid → 4-[({4-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(methyl)amino]piperidine-4-carboxylic acid

HRID 1867686Notes

Reaction equation

HRID 1867686 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([N:17]([CH2:19][C:20]2[CH:21]=[C:22]3[C:27](=[CH:28][C:29]=2[O:30][CH3:31])[N:26]=[CH:25][N:24]=[C:23]3[NH:32][C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([Cl:39])[C:34]=2[F:40])[CH3:18])([C:14]([OH:16])=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>O1CCOCC1>[Cl:39][C:35]1[C:34]([F:40])=[C:33]([NH:32][C:23]2[C:22]3[C:27](=[CH:28][C:29]([O:30][CH3:31])=[C:20]([CH2:19][N:17]([CH3:18])[C:11]4([C:14]([OH:16])=[O:15])[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]4)[CH:21]=3)[N:26]=[CH:25][N:24]=2)[CH:38]=[CH:37][CH:36]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 690474061-(Tert-butoxycarbonyl)-4-[({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(methyl)amino]piperidine-4-carboxylic acid

Product 1

HCID 690481224-[({4-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(methyl)amino]piperidine-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1-(tert-butoxycarbonyl)-4-[({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(methyl)amino]piperidine-4-carboxylic acid (prepared as described in Example 16) was deprotected by treating the compound with hydrogen chloride in dioxane using an analogous method to that described for the equivalent step in Example 7 to give 4-[({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(methyl)amino]piperidine-4-carboxylic acid; 1H NMR Spectrum: (DMSO-d6+CD3COOD) 2.06 (m, 2H); 2.15 (m, 2H); 2.26 (s, 3H); 3.04 (m, 2H); 3.27 (m, 2H); 3.75 (s, 2H); 3.96 (s, 3H); 7.21 (s, 1H); 7.28 (m, 1H); 7.48 (m, 1H); 7.54 (m, 1H); 8.32 (s, 1H); 8.42 (S, 1H). Mass Spectrum: (M+H)+ 474.

Sources & evidence

ORD record
ord-6a1bf733d51846e088ac8b2040da8a84
Source dataset
uspto-grants-2009_12
Patent number
US07632840B2

Reaction notes

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