Acetic Acid → HCID 24964376, compound

HRID 1161869Notes

Reaction equation

HRID 1161869 reaction equation
[C:1]([NH:5][C:6](=[O:33])[CH2:7][N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([N:19]3[CH2:25][CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[CH:15]=2)[N:10]=[C:9]1[C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[CH:27]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:34][C:35]([CH3:37])=O.C([BH3-])#N.[Na+].C(O)(=O)C>C1COCC1>[C:1]([NH:5][C:6](=[O:33])[CH2:7][N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([N:19]3[CH2:25][CH2:24][CH2:23][N:22]([CH:35]([CH3:37])[CH3:34])[CH2:21][CH2:20]3)[CH:15]=2)[N:10]=[C:9]1[C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[CH:27]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 5003444Sodium cyanoborohydrideHCID 24965796HCID 24965796, compound

Product 1

HCID 24964376HCID 24964376, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-tert-Butyl-2-[2-(3-chlorophenyl)-4-oxo-6-perhydro-1,4-diazepin-1-yl-4H-quinazolin-3-yl]acetamide (EXAMPLE 1a) (17 mg, 0.03 mmol), anhydrous acetone (30 μL), sodium cyanoborohydride (3 mg, 0.03 mmol) and glacial acetic acid (12 μL, 0.21 mmol) in anhydrous THF (0.15 mL) was heated in a microwave at 130° C. for 10 minutes. The resulting mixture was purified by preparative TLC on silica gel with DCM:MeOH:NH4OH (40:2:1, v/v) as eluent to give N-tert-butyl-2-[2-(3-chlorophenyl)-6-(4-isopropylperhydro-1,4-diazepin-1-yl)-4-oxo-4H-quinazolin-3-yl]acetamide (EXAMPLE 5a) (7.1 mg, 0.014 mmol, 47%).

Workup

  1. customThe resulting mixture was purified by preparative TLC on silica gel with DCM:MeOH:NH4OH (40:2:1

Sources & evidence

ORD record
ord-bccbc2ff46174427b198e57952e7825c
Source dataset
uspto-grants-2010_10
Patent number
US07820649B2

Reaction notes

Loading…