Dimethylformamide → Trifluoroacetate

HRID 1914744Notes

Reaction equation

HRID 1914744 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:26][C:27]([F:30])([F:29])[F:28])=[C:6]([NH:8][C:9]2[N:18]=[CH:17][C:16]3[CH2:15][CH2:14][C:13]4[C:19]([C:23]([NH2:25])=[O:24])=[N:20][N:21]([CH3:22])[C:12]=4[C:11]=3[N:10]=2)[CH:7]=1.CN(C)C=O.CCN(C(C)C)C(C)C.[C:45]([N:52]1[CH2:59][CH2:58][CH2:57][C@H:53]1[C:54](O)=[O:55])([O:47]C(C)(C)C)=[O:46]>O>[NH:52]1[CH2:59][CH2:58][CH2:57][CH:53]1[C:54]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([O:26][C:27]([F:29])([F:28])[F:30])=[C:6]([NH:8][C:9]2[N:18]=[CH:17][C:16]3[CH2:15][CH2:14][C:13]4[C:19]([C:23]([NH2:25])=[O:24])=[N:20][N:21]([CH3:22])[C:12]=4[C:11]=3[N:10]=2)[CH:7]=1)=[O:55].[F:30][C:27]([F:28])([F:29])[C:45]([O-:47])=[O:46]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 52943186HCID 52943186, compound

Product 2

HCID 84468TrifluoroacetateYield 499.9%HCID 68668492HCID 68668492, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 8-(5-amino-2-trifluoromethoxy-phenylamino)-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide (146 mg, 0.4 mmol) in anhydrous dimethylformamide (5 mL) TBTU (190 g, 0.6 mmol) HOBT (81 mg, 0.6 mmol), and DIPEA (0.104 ml, 0.6 mmol) were added. The mixture was stirred at room temperature for 30 minutes. Then BOC-L-proline (129 mg, 0.6 mmol) was added and the reaction was stirred for an additional 3 h. The reaction mixture was diluted with water and the precipitate was collected, diluted with DCM (10 mL) and treated with TFA (1 mL). Evaporation of the solvent gave the title compound as trifluoroacetate salt (113 mg, 44% yield).

Workup

  1. additionwere added
  2. stirringthe reaction was stirred for an additional 3 h
  3. customthe precipitate was collected
  4. additiondiluted with DCM (10 mL)
  5. additiontreated with TFA (1 mL)
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-05f1f13a91894794b8c77913687ea750
Source dataset
uspto-grants-2013_12
Patent number
US08614220B2

Reaction notes

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