Isopropylamine → HCID 66907341, compound

HRID 1690480Notes

Reaction equation

HRID 1690480 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:46])[CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][C:32]3[C:41]4[C:36](=[CH:37][C:38]([O:44][CH3:45])=[C:39]([O:42][CH3:43])[CH:40]=4)[N:35]=[CH:34][N:33]=3)=[CH:27][CH:26]=2)=[CH:18][C:17]=1[CH:47]=O.[CH:49]([NH2:52])([CH3:51])[CH3:50].C(OC)(OC)OC>C(Cl)Cl.CO>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:46])[CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][C:32]3[C:41]4[C:36](=[CH:37][C:38]([O:44][CH3:45])=[C:39]([O:42][CH3:43])[CH:40]=4)[N:35]=[CH:34][N:33]=3)=[CH:27][CH:26]=2)=[CH:18][C:17]=1[CH2:47][NH:52][CH:49]([CH3:51])[CH3:50]

Participants

7

Reactant 4

HCID 6363IsopropylamineHCID 9005Trimethyl orthoformateHCID 5049666Sodium triacetoxyborohydrideHCID 86634409HCID 86634409, compound

Product 1

HCID 66907341HCID 66907341, compoundYield 35.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Sodium triacetoxyborohydride (0.072 g) was added portionwise to a stirred mixture of N-(4-chloro-3-formylphenyl)-2-[4-(6,7-dimethoxyquinazolin-4-oxy)phenyl]acetamide (0.08 g), isopropylamine (0.021 g), trimethyl orthoformate (0.2 ml), methanol (0.2 ml) and methylene chloride (0.6 ml) and the resultant mixture was stirred at ambient temperature for 12 hours. The mixture was evaporated and the residue was purified by preparative HPLC using a Waters ‘β Basic Hypersil’ reversed-phase column (5 microns silica, 20 mm diameter, 100 mm length) and decreasingly polar mixtures of water (containing 0.2% ammonium carbonate) and acetonitrile as eluent. There was thus obtained the title compound as a solid (0.031 g); 1H NMR: (DMSOd6) 1.03 (d, 6H), 1.88 (br s, 1H), 2.71-2.8 (m, 1H), 3.7 (s, 2H), 3.72 (br s, 2H), 3.97 (s, 3H), 3.99 (s, 3H), 7.26 (d, 2H), 7.32 (d, 1H), 7.39 (s, 1H), 7.44 (d, 2H), 7.55 (s, 1H), 7.64 (m, 1H), 7.73 (d, 1H), 8.53 (s, 1H), 10.34 (s, 1H); Mass Spectrum: M+H+ 521 and 523.

Workup

  1. customThe mixture was evaporated
  2. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-72cff9be5be04d8ba4a26ce640c15e2b
Source dataset
uspto-grants-2012_04
Patent number
US08153643B2

Reaction notes

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