Ammonia → HCID 67024573, compound

HRID 488420Notes

Reaction equation

HRID 488420 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[C:5]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:43][CH3:44])=[C:17]([NH:20][C:21](=[O:42])[CH:22]=[CH:23][CH2:24][N:25]([CH2:34][CH:35](OCC)[O:36][CH2:37][CH3:38])[CH2:26][CH:27]([O:31][CH2:32][CH3:33])[O:28]CC)[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1.N>>[Br:2][C:3]1[CH:4]=[C:5]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:43][CH3:44])=[C:17]([NH:20][C:21](=[O:42])[CH:22]=[CH:23][CH2:24][N:25]4[CH2:26][CH:27]([O:31][CH2:32][CH3:33])[O:28][CH:35]([O:36][CH2:37][CH3:38])[CH2:34]4)[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 54107588HCID 54107588, compound

Product 1

HCID 67024573HCID 67024573, compound

Procedure

1 ml of ice-cooled concentrated hydrochloric acid is added to 340 mg of 4-[(3-bromophenyl)amino]-6-((4-[N,N-bis(2,2-diethyoxyethyl)amino]-1-oxo-2-buten-1-yl)amino)-7-methoxy-quinazoline while cooling with an ice bath. The mixture is left to stand for 3 hours before 1.5 ml of concentrated ammonia solution is added dropwise while cooling with an ice bath for working up. The precipitate formed is suction filtered and washed with water. The crude product is purified by chromatography on a silica gel column with methylene chloride/methanol (20:1) Yield: 50 mg (17% of theory) Melting point: 133-138° C. Mass spectrum (EI): m/z=585, 587 [M]+

Workup

  1. temperaturewhile cooling with an ice bath
  2. waitThe mixture is left
  3. additionis added dropwise
  4. temperaturewhile cooling with an ice bath
  5. customThe precipitate formed
  6. filtrationfiltered
  7. washwashed with water
  8. customThe crude product is purified by chromatography on a silica gel column with methylene chloride/methanol (20:1) Yield: 50 mg (17% of theory) Melting point: 133-138° C

Sources & evidence

ORD record
ord-82a173af1eb34543aa1f8e023e3444f4
Source dataset
uspto-grants-2005_12
Patent number
US06972288B1

Reaction notes

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