Methylamine → HCID 13225517, compound

HRID 1979572Notes

Reaction equation

HRID 1979572 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]2[CH2:6][N:7]=[C:8]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[F:24])[C:9]3[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:10]=3[C:11]=2[N:12]=1.[CH3:25][NH2:26]>CN(C)C=O>[Cl:17][C:15]1[CH:14]=[CH:13][C:10]2[C:11]3[N:12]=[C:2]([NH:26][CH3:25])[N:3]=[CH:4][C:5]=3[CH2:6][N:7]=[C:8]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[F:24])[C:9]=2[CH:16]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 13225515HCID 13225515, compound

Product 1

HCID 13225517HCID 13225517, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1 g(0.00279 mol) of 2,9-dichloro-7-(2-fluorophenyl)-5H-pyrimido[5,4-d][2]benzazepine in 4 ml of N,N-dimethylformamide was cooled in an ice bath and saturated with methylamine. After 64 hr at room temperature, 50 ml of ice water was added and the reaction was filtered. The precipitated was partitioned between 50 ml ofdichloromethane and 50 ml of water, and the organic layer was washed with 25 ml of brine solution, dried and evaporated to dryness. The oil was crystallized from ether and then recrystallized from dichloromethane/ether and then from methanol to give the end product as white prisms, mp 172°-179°.

Workup

  1. filtrationthe reaction was filtered
  2. customThe precipitated was partitioned between 50 ml ofdichloromethane and 50 ml of water
  3. washthe organic layer was washed with 25 ml of brine solution
  4. customdried
  5. customevaporated to dryness
  6. customThe oil was crystallized from ether
  7. customrecrystallized from dichloromethane/ether

Sources & evidence

ORD record
ord-f0da3e9933f3477c8501c5d12bb27218
Source dataset
uspto-grants-1984_11
Patent number
US04481142

Reaction notes

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