Trifluoroacetic acid → HCID 77981585, compound

HRID 716045Notes

Reaction equation

HRID 716045 reaction equation
[C:1]([C:3](=[CH:9][C:10]1[CH:11]=[N:12][C:13]([NH:16][C:17]2[N:18]=[C:19]3[C:25]([C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:24][N:23](COCC[Si](C)(C)C)[C:20]3=[N:21][CH:22]=2)=[CH:14][CH:15]=1)[C:4]([N:6]([CH3:8])[CH3:7])=[O:5])#[N:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:1]([C:3](=[CH:9][C:10]1[CH:11]=[N:12][C:13]([NH:16][C:17]2[N:18]=[C:19]3[C:25]([C:26](=[O:31])[C:27]([CH3:29])([CH3:28])[CH3:30])=[CH:24][NH:23][C:20]3=[N:21][CH:22]=2)=[CH:14][CH:15]=1)[C:4]([N:6]([CH3:7])[CH3:8])=[O:5])#[N:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 710142952-cyano-N,N-dimethyl-3-(6-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)pyridin-3-yl)acrylamide

Product 1

HCID 77981585HCID 77981585, compoundYield 52.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 25 ml one necked round bottom flask 2-cyano-N,N-dimethyl-3-(6-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)pyridin-3-yl)acrylamide (0.1 g, 0.000182 mole) was taken in CH2Cl2 (10 ml). To this reaction mixture TFA (2.0 ml) was added dropwise at 0° C. After completion of the addition, the reaction mixture was warmed up to RT and then stirred for 16 hrs. After completion of the reaction, CH2Cl2 was distilled out and set pH 8 to 9 using saturated NaHCO3 solution (20.0 ml) at 5° C. Reaction mixture was stirred for 15 min. The solid was filtered, washed with methanol followed by n-pentane and dried under vacuum to yield 40 mg of 2-cyano-N,N-dimethyl-3-(6-(7-pivaloyl-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)pyridin-3-yl)acrylamide.

Workup

  1. additionAfter completion of the addition
  2. distillationwas distilled out
  3. customat 5° C
  4. customReaction mixture
  5. stirringwas stirred for 15 min
  6. filtrationThe solid was filtered
  7. washwashed with methanol
  8. customdried under vacuum

Sources & evidence

ORD record
ord-9d82f8985d93478baa27fa8b90df75d5
Source dataset
uspto-grants-2015_11
Patent number
US09187487B2

Reaction notes

Loading…