Trifluoroacetic acid → HCID 67024915, compound

HRID 488422Notes

Reaction equation

HRID 488422 reaction equation
FC(F)(F)C(O)=O.[Br:8][C:9]1[CH:10]=[C:11]([NH:15][C:16]2[C:25]3[C:20](=[CH:21][C:22]([O:44][CH3:45])=[C:23]([NH:26][C:27](=[O:43])[CH:28]=[CH:29][CH2:30][N:31]([CH2:35][C:36]([O:38]C(C)(C)C)=[O:37])[CH2:32][CH2:33][OH:34])[CH:24]=3)[N:19]=[CH:18][N:17]=2)[CH:12]=[CH:13][CH:14]=1>C(Cl)Cl>[Br:8][C:9]1[CH:10]=[C:11]([NH:15][C:16]2[C:25]3[C:20](=[CH:21][C:22]([O:44][CH3:45])=[C:23]([NH:26][C:27](=[O:43])[CH:28]=[CH:29][CH2:30][N:31]([CH2:35][C:36]([OH:38])=[O:37])[CH2:32][CH2:33][OH:34])[CH:24]=3)[N:19]=[CH:18][N:17]=2)[CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67024584HCID 67024584, compound

Product 1

HCID 67024915HCID 67024915, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1 ml of trifluoroacetic acid is added dropwise within two minutes to a solution of 330 mg of 4-[(3-bromophenyl)amino]-6-[(4-{N-[(tert-butyloxycarbonyl)methyl]-N-(2-hydroxyethyl)amino}-1-oxo-2-buten-1-yl)amino]-7-methoxy-quinazoline in 4 ml of methylene chloride while cooling with an ice bath. The reaction mixture is stirred for half an hour while cooling with an ice bath and then for a further 24 hours at ambient temperature. For working up, the mixture is evaporated to dryness in the rotary evaporator. The crude product is stirred with ethyl acetate, the solid precipitate is filtered off, washed with ethyl acetate and dried in vacuo at 50° C. Yield: 169 mg (57% of theory), Rf value: 0.50 (Reversed phase ready-made TLC plate (E. Merck), acetonitrile/water/trifluoroactic acid=50:50:1) Mass spectrum (ESI−): m/z=528, 530 [M−H]−

Workup

  1. temperaturewhile cooling with an ice bath
  2. temperaturewhile cooling with an ice bath
  3. customthe mixture is evaporated to dryness in the rotary evaporator
  4. stirringThe crude product is stirred with ethyl acetate
  5. filtrationthe solid precipitate is filtered off
  6. washwashed with ethyl acetate
  7. customdried in vacuo at 50° C

Sources & evidence

ORD record
ord-4ae29036514341edbab323cc770e17e7
Source dataset
uspto-grants-2005_12
Patent number
US06972288B1

Reaction notes

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