Formaldehyde → HCID 57979831, compound

HRID 1867764Notes

Reaction equation

HRID 1867764 reaction equation
[C:1](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:15][C:16]1[C:17]([F:44])=[C:18]([NH:22][C:23]2[C:32]3[C:27](=[CH:28][C:29]([O:42][CH3:43])=[C:30]([CH2:33][NH:34][C:35]([CH3:41])([C:37]([NH:39][CH3:40])=[O:38])[CH3:36])[CH:31]=3)[N:26]=[CH:25][N:24]=2)[CH:19]=[CH:20][CH:21]=1.C=O>C(O)(=O)C.ClCCl>[Cl:15][C:16]1[C:17]([F:44])=[C:18]([NH:22][C:23]2[C:32]3[C:27](=[CH:28][C:29]([O:42][CH3:43])=[C:30]([CH2:33][N:34]([CH3:1])[C:35]([CH3:41])([C:37]([NH:39][CH3:40])=[O:38])[CH3:36])[CH:31]=3)[N:26]=[CH:25][N:24]=2)[CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 57979839HCID 57979839, compound

Product 1

HCID 57979831HCID 57979831, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 21922555Acetic acid methylene chlorideSolvent

Procedure

Solid sodium triacetoxy borohydride (0.2 g, 0.94 mmol) was added to a stirred solution of N2-({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)-N1,2-dimethylalaninamide (0.12 g, 0.28 mmol Example 95) in a mixture of acetic acid/dichloromethane (10 ml, 5% v/v) and in the presence of type 4 Å molecular sieves, followed rapidly by aqueous formaldehyde (1 ml). After 10 minutes the reaction mixture was concentrated and purified by preparative LCMS (standard basic system) to give the title product as a white solid, (0.085 g, 69%); 1H NMR Spectrum: (DMSO d6) 1.24 (s, 6H), 2.18 (s, 3H), 2.65 (d, 3H), 3.52 (s, 2H), 3.96 (s, 3H), 7.20 (s, 1H), 7.29 (t, 1H), 7.52-7.62 (m, 2H), 7.79 (m, 1H), 8.44 (m, 2H), 9.78 (s, 1H); Mass Spectrum: (M+H)+ 446.

Workup

  1. concentrationAfter 10 minutes the reaction mixture was concentrated
  2. custompurified by preparative LCMS (standard basic system)

Sources & evidence

ORD record
ord-ac47cb74e1d5494d87995e73361cb4a2
Source dataset
uspto-grants-2009_12
Patent number
US07632840B2

Reaction notes

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