Trifluoroacetic acid → HCID 86679620, compound

HRID 577674Notes

Reaction equation

HRID 577674 reaction equation
C(O)(C(F)(F)F)=O.[CH3:8][N:9]1[CH:13]=[C:12]([NH:14][C:15]2[N:16]=[C:17]([O:32][CH2:33][C@H:34]3[C@H:38]([CH3:39])[CH2:37][NH:36][CH2:35]3)[C:18]3[CH:23]=[CH:22][N:21]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:19]=3[N:20]=2)[CH:11]=[N:10]1.CCN(C(C)C)C(C)C.[C:49](Cl)(=[O:52])[CH:50]=[CH2:51]>C(Cl)Cl.C(Cl)Cl.CO>[CH3:39][C@H:38]1[C@H:34]([CH2:33][O:32][C:17]2[C:18]3[CH:23]=[CH:22][N:21]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:19]=3[N:20]=[C:15]([NH:14][C:12]3[CH:11]=[N:10][N:9]([CH3:8])[CH:13]=3)[N:16]=2)[CH2:35][N:36]([C:49](=[O:52])[CH:50]=[CH2:51])[CH2:37]1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 13140Acryloyl chlorideHCID 81531DiisopropylethylamineHCID 86679619HCID 86679619, compound

Product 1

HCID 86679620HCID 86679620, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of the TFA salt of N-(1-methyl-1H-pyrazol-4-yl)-4-{[trans-4-methylpyrrolidin-3-yl]methoxy}-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-2-amine (0.9 g, 1.61 mmol) in dry DCM (20 mL) were added DIPEA (1.25 g, 9.7 mmol) and acryloyl chloride (144.9 mg, 1.61 mmol) at rt. After the addition, the reaction mixture was stirred at rt for 1 hr. TLC(CH2Cl2/MeOH=10:1) showed the reaction was complete. The reaction mixture was diluted with DCM (10 mL), washed with water (10 mL), brine (10 mL), dried over Na2SO4 and concentrated to yield the title compound (0.82 g, 100% yield) as a brown solid.

Workup

  1. additionAfter the addition
  2. washwashed with water (10 mL), brine (10 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8e0349e6fa5a4f519e8e506f877df52b
Source dataset
uspto-grants-2015_05
Patent number
US09040547B2

Reaction notes

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