Trifluoroacetic acid → HCID 117902863, compound

HRID 923670Notes

Reaction equation

HRID 923670 reaction equation
C(O[C:6](=O)[N:7]([CH:9]([C:11](=[O:42])[NH:12][C:13]1[CH:18]=[C:17]([C:19]2[C:20]3[N:27]([CH3:28])[N:26]=[C:25]([CH3:29])[C:21]=3[N:22]=[CH:23][N:24]=2)[CH:16]=[C:15]([C:30]#[C:31][C:32]2[CH:33]=[C:34]3[C:38](=[CH:39][CH:40]=2)[N:37]([CH3:41])[N:36]=[CH:35]3)[N:14]=1)[CH3:10])C)(C)(C)C.C(O)(C(F)(F)F)=O.C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH3:28][N:27]1[C:20]2[C:19]([C:17]3[CH:16]=[C:15]([C:30]#[C:31][C:32]4[CH:33]=[C:34]5[C:38](=[CH:39][CH:40]=4)[N:37]([CH3:41])[N:36]=[CH:35]5)[N:14]=[C:13]([NH:12][C:11](=[O:42])[CH:9]([NH:7][CH3:6])[CH3:10])[CH:18]=3)=[N:24][CH:23]=[N:22][C:21]=2[C:25]([CH3:29])=[N:26]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 117911045HCID 117911045, compound

Product 1

HCID 117902863HCID 117902863, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl-N-{1-[(4-{1,3-dimethyl-1H-pyrazolo[4,3-d]pyrimidin-7-yl}-6-[2-(1-methyl-1H-indazol-5-yl)ethynyl]pyridin-2-yl)carbamoyl]ethyl}-N-methylcarbamate H1 (246 mg, 0.42 mmol), DCM (5 ml) and TFA (1 ml) is stirred at RT for 1 h. 50 ml of a saturated aqueous sodium hydrogencarbonate solution is added and the mixture extracted with DCM. The combined organic layers are dried over MgSO4 and concentrated in vacuo. The product is purified by RP HPLC. Yield: 99 mg (49%). HPLC-MS: M+H=480; tR=1.16 min (METHOD—1).

Workup

  1. extractionthe mixture extracted with DCM
  2. dry with materialThe combined organic layers are dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe product is purified by RP HPLC

Sources & evidence

ORD record
ord-bf36ce12994e4239a470608cdc115429
Source dataset
uspto-grants-2016_03
Patent number
US09278978B2

Reaction notes

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