Formamide → HCID 10994090, compound

HRID 342224Notes

Reaction equation

HRID 342224 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]([C:20]([C:22]3[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=3)=[N: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 10994090HCID 10994090, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of 230 mg of [2-amino-4-[6-(allyl-methyl-amino)-hexyloxy]-phenyl]-(4-bromo-phenyl)-methanone in 0.5 ml of formic acid and 2 ml of formamide is boiled at 165° C. for 25 min., then concentrated and converted into the free amine (title compound) with methylene chloride/saturated sodium bicarbonate solution. After purification (silica gel, methylene chloride/methanol 2.5% to 10%) the residue is dissolved in methylene chloride/ether and treated with 23.7 mg of fumaric acid. After stirring and filtration there are obtained 30 mg of allyl-[6-[4-(4-bromo-phenyl)-quinazolin-7-yloxy]-hexyl]-methyl-amine.fumarate (1:1), m.p 90°-95° C., MS: m/e 454 (M+H+, 1 Br).

Workup

  1. customfor 25 min.
  2. concentrationconcentrated
  3. customAfter purification (silica gel, methylene chloride/methanol 2.5% to 10%) the residue
  4. dissolutionis dissolved in methylene chloride/ether
  5. additiontreated with 23.7 mg of fumaric acid
  6. filtrationfiltration there

Sources & evidence

ORD record
ord-1c996b4a6d7e42efb4d59ec0518ec6f7
Source dataset
uspto-grants-1999_01
Patent number
US05856503

Reaction notes

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