Hydrochloric Acid → HCID 68638800, compound

HRID 640010

Reaction equation

HRID 640010 reaction equation
FC(F)(F)C(OC1C(F)=C(F)C(F)=C(F)C=1F)=O.[Cl:19][CH2:20][CH2:21][CH2:22][O:23][C:24]1[CH:33]=[C:32]2[C:27]([C:28]([NH:34][C:35]3[CH:36]=[N:37][N:38]([CH2:40][C:41](O)=[O:42])[CH:39]=3)=[N:29][CH:30]=[N:31]2)=[CH:26][CH:25]=1.N1C=CC=CC=1.[NH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1.Cl>CN(C)C=O>[Cl:19][CH2:20][CH2:21][CH2:22][O:23][C:24]1[CH:33]=[C:32]2[C:27]([C:28]([NH:34][C:35]3[CH:36]=[N:37][N:38]([CH2:40][C:41]([NH:50][C:51]4[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=4)=[O:42])[CH:39]=3)=[N:29][CH:30]=[N:31]2)=[CH:26][CH:25]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6115AnilineHCID 4327891Pentafluorophenyl TrifluoroacetateHCID 68638745(4-{[7-(3-chloropropoxy)quinazolin-4-yl]amino}-1H-pyrazol-1-yl)acetic acid

Product 1

HCID 68638800HCID 68638800, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Pentafluorophenyl trifluoroacetate (0.867 g, 3.10 mmol) was added dropwise, at room temperature, to a stirred suspension of (4-{[7-(3-chloropropoxy)quinazolin-4-yl]amino}-1H-pyrazol-1-yl)acetic acid (0.800 g, 2.21 mmol) and pyridine (0.245 g, 3.10 mmol) in dimethylformamide (8 ml). After stirring for 5 minutes, aniline (0.412 g, 4.43 mmol) was added and the reaction mixture was stirred for 2 hours. The mixture was poured into dilute hydrochloric acid (0.2N, 25 ml) and the resultant solid filtered and then washed with water. The residue was stirred in dilute aqueous sodium hydroxide solution and filtered and the residue washed successively with water, methanol and diethylether to give 2-(4-{[7-(3-chloropropoxy)quinazolin-4-yl]amino}-1H-pyrazol-1-yl)-N-phenylacetamide (0.520 g, 54% yield): MS (+ve ESI): 437 (M+H)+.

Workup

  1. stirringthe reaction mixture was stirred for 2 hours
  2. filtrationthe resultant solid filtered
  3. washwashed with water
  4. stirringThe residue was stirred in dilute aqueous sodium hydroxide solution
  5. filtrationfiltered
  6. washthe residue washed successively with water, methanol and diethylether

Sources & evidence

ORD record
ord-1f300c464cdb4f23aa328beff88a23fd
Source dataset
uspto-grants-2010_04
Patent number
US07691867B2

Linked notes

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