Trifluoroacetic acid → 3-Bromo-4-(7-(cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-ylamino)benzonitrile 2,2,2-trifluoroacetate

HRID 2037017Notes

Reaction equation

HRID 2037017 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][C:3]=1[NH:10][C:11]1[CH:16]=[C:15]([N:17]([CH:25]2[CH2:27][CH2:26]2)C(=O)OC(C)(C)C)[N:14]2[N:28]=[CH:29][C:30]([CH:31]=[O:32])=[C:13]2[N:12]=1.[F:33][C:34]([F:39])([F:38])[C:35]([OH:37])=[O:36]>ClCCl>[F:33][C:34]([F:39])([F:38])[C:35]([OH:37])=[O:36].[Br:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]=1[NH:10][C:11]1[CH:16]=[C:15]([NH:17][CH:25]2[CH2:26][CH2:27]2)[N:14]2[N:28]=[CH:29][C:30]([CH:31]=[O:32])=[C:13]2[N:12]=1)[C:8]#[N:9]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86714612Tert-butyl 5-(2-bromo-4-cyanophenylamino)-3-formylpyrazolo[1,5-a]pyrimidin-7-yl(cyclopropyl)carbamate

Product 1

HCID 867146133-Bromo-4-(7-(cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-ylamino)benzonitrile 2,2,2-trifluoroacetateYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl 5-(2-bromo-4-cyanophenylamino)-3-formylpyrazolo[1,5-a]pyrimidin-7-yl(cyclopropyl)carbamate (105 mg, 0.21 mmol) was dissolved in dichloromethane (2 mL) and trifluoroacetic acid (2 mL) was added. After 1 h, the reaction was concentrated to dryness and the residue was triturated with Et2O. The yellow solid was collected and dried to give 3-bromo-4-(7-(cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-ylamino)benzonitrile 2,2,2-trifluoroacetate (72 mg, 67%).

Workup

  1. concentrationthe reaction was concentrated to dryness
  2. customthe residue was triturated with Et2O
  3. customThe yellow solid was collected
  4. customdried

Sources & evidence

ORD record
ord-511f81fefd414d0b92d9430edcf21e62
Source dataset
uspto-grants-2013_11
Patent number
US08575177B2

Reaction notes

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