Formamide → HCID 178457214, compound

HRID 342226Notes

Reaction equation

HRID 342226 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]([CH2:17][CH:18]=[CH2:19])[CH3:16])[CH:5]=[CH:4][C:3]=1[C:20]([C:22]1[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=1)=O.[CH:29]([NH2:31])=O>C(O)=O>[CH2:17]([N:15]([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][O:8][C:6]1[CH:7]=[C:2]2[C:3]([CH:20]([C:22]3[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=3)[NH:31][CH:29]=[N:1]2)=[CH:4][CH:5]=1)[CH3:16])[CH:18]=[CH2:19]

Participants

4

Reactant 2

HCID 713FormamideHCID 10873957HCID 10873957, compound

Product 1

HCID 178457214HCID 178457214, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of 445 mg of [2-amino-4-[6-(allyl-methyl-amino)-hexyloxy]-phenyl]-(4-bromo-phenyl)-methanone in 1 ml of formic acid and 4 ml of formamide is boiled at 160° C. for 35 hrs., then concentrated and converted into the free amine (title compound) with sodium bicarbonate solution saturated with methylene chloride. The residue is dissolved in methylene chloride/ether and treated with 73 mg of fumaric acid. After stirring the mixture is decanted and the residue is triturated with ether and filtered off. There are obtained 30 mg of (RS)-allyl-[6-[4-(4-bromo-phenyl)-3,4-dihydro-quinazolin-7-yloxy]-hexyl]-methyl-amine.fumarate (1:1), m.p 120° C. (decomposition), MS: m/e 456 (M+H+, 1 Br).

Workup

  1. customfor 35 hrs
  2. concentration, then concentrated
  3. dissolutionThe residue is dissolved in methylene chloride/ether
  4. additiontreated with 73 mg of fumaric acid
  5. customis decanted
  6. customthe residue is triturated with ether
  7. filtrationfiltered off

Sources & evidence

ORD record
ord-317c989cb5ca4eb9976081f20dd6f547
Source dataset
uspto-grants-1999_01
Patent number
US05856503

Reaction notes

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