Formic Acid → HCID 11687906, compound

HRID 1668806Notes

Reaction equation

HRID 1668806 reaction equation
[CH:1]([OH:3])=O.C(OC(=O)C)(=O)C.[CH3:11][N:12]([C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:23]=[C:22]([CH3:30])[N:21]=1)[C:13]1[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=1>C(Cl)Cl>[CH3:11][N:12]([C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:23]=[C:22]([CH3:30])[N:21]=1)[C:13]1[CH:14]=[CH:15][C:16]([NH:19][CH:1]=[O:3])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 11311597N-methyl-N-(2-methylquinazolin-4-yl)benzene-1,4-diamine

Product 1

HCID 11687906HCID 11687906, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of formic acid 1 mL and acetic anhydride 1 mL, stirred at room temperature for 1 h, was added a solution of N-methyl-N-(2-methylquinazolin-4-yl)benzene-1,4-diamine 0.132 g (0.5 mmol) in CH2Cl2 5 mL dropwise at 0° C. The reaction mixture was stirred at room temperature for 16 h. After concentration, the crude product was purified by recrystallization in EtOAc/MeOH to give the titled compound in 85% yield. The compound was further purified with preparative HPLC for analytical uses. 1H NMR (CD3OD, 400 MHz): δ 7.84-7.79 (m, 2H), 7.71-7.65 (m, 1H), 7.44-7.41 (m, 1H), 7.27-7.28 (m, 2H), 7.02-6.99 (m, 2H), [3.84 (s, 1H), 3.81 (s, 2H)], [2.78 (s, 1H), 2.76 (s, 2H)] (Two isomers were observed in 2:1 ratio.). m/e: 293.1438 (M+1).

Workup

  1. concentrationAfter concentration
  2. customthe crude product was purified by recrystallization in EtOAc/MeOH

Sources & evidence

ORD record
ord-003d9f31441c4849b6b2becd30d6db37
Source dataset
uspto-grants-2011_08
Patent number
US07989462B2

Reaction notes

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