Acetonitrile → HCID 117899555, compound

HRID 522287Notes

Reaction equation

HRID 522287 reaction equation
FC(F)(F)C(O)=O.[C:8]([C:10]1[N:11]=[C:12]([C:20]2[CH:21]=[C:22]([C:42]([F:45])([F:44])[F:43])[C:23]([O:26][CH2:27][CH2:28][O:29][C@@H:30]3[CH2:34][CH2:33][N:32](C(OC(C)(C)C)=O)[CH2:31]3)=[N:24][CH:25]=2)[C:13]2[CH:18]=[CH:17][N:16]([CH3:19])[C:14]=2[N:15]=1)#[N:9].C(#N)C.C(Cl)[Cl:50]>>[ClH:50].[CH3:19][N:16]1[C:14]2[N:15]=[C:10]([C:8]#[N:9])[N:11]=[C:12]([C:20]3[CH:25]=[N:24][C:23]([O:26][CH2:27][CH2:28][O:29][C@@H:30]4[CH2:34][CH2:33][NH:32][CH2:31]4)=[C:22]([C:42]([F:44])([F:45])[F:43])[CH:21]=3)[C:13]=2[CH:18]=[CH:17]1

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 117914141HCID 117914141, compound

Product 1

HCID 117899555HCID 117899555, compound

Procedure

Trifluoroacetic acid (2 mL) was added to a solution of tert-butyl(3R)-3-(2-{[5-(2-cyano-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-3-(trifluoromethyl)pyridin-2-yl]oxy}ethoxy)pyrrolidine-1-carboxylate (240 mg) in CH2Cl2 (4 mL)-acetonitrile (1 mL) at room temperature, and the mixture was stirred at the same temperature for 1 hour. After the reaction mixture was concentrated under reduced pressure, CH2Cl2 (4 mL) and a 4 M solution of hydrogen chloride in EtOAc (0.4 mL) were added to the residue at room temperature. The reaction mixture was concentrated under reduced pressure, and diisopropyl ether was added to the residue. The precipitate was collected by filtration, whereby 7-methyl-4-[6-{2-[(3R)-pyrrolidin-3-yloxy]ethoxy}-5-(trifluoromethyl)pyridin-3-yl]-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile monohydrochloride (208 mg) was obtained as a solid.

Workup

  1. concentrationAfter the reaction mixture was concentrated under reduced pressure, CH2Cl2 (4 mL)
  2. additiona 4 M solution of hydrogen chloride in EtOAc (0.4 mL) were added to the residue at room temperature
  3. concentrationThe reaction mixture was concentrated under reduced pressure, and diisopropyl ether
  4. additionwas added to the residue
  5. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-c829aa09c65f41f6bb706d796b9881cc
Source dataset
uspto-grants-2016_05
Patent number
US09328118B2

Reaction notes

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