Diethyl Ether → Trifluoroacetic acid

HRID 591355Notes

Reaction equation

HRID 591355 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][N:8]2[CH:11]2[CH2:16][CH2:15][N:14]([C:17]([NH:19][C:20]3[S:21][C:22]4[CH2:23][N:24](C(OC(C)(C)C)=O)[CH2:25][CH2:26][C:27]=4[N:28]=3)=[O:18])[CH2:13][CH2:12]2)=[CH:4][CH:3]=1.[C:36]([OH:42])([C:38]([F:41])([F:40])[F:39])=[O:37].CCOCC>C(Cl)Cl>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][N:8]2[CH:11]2[CH2:12][CH2:13][N:14]([C:17]([NH:19][C:20]3[S:21][C:22]4[CH2:23][NH:24][CH2:25][CH2:26][C:27]=4[N:28]=3)=[O:18])[CH2:15][CH2:16]2)=[CH:4][CH:3]=1.[C:36]([OH:42])([C:38]([F:41])([F:40])[F:39])=[O:37]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 6422Trifluoroacetic acidHCID 89626925HCID 89626925, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 71657445HCID 71657445, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-(4-(6-fluoroindolin-1-yl)piperidine-1-carboxamido)-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate (501 mg, 1.0 mmol) in CH2Cl2 (2 mL) was added TFA (1 mL) dropwise at room temperature. The resulting mixture was stirred at room temperature for 45 min and then Et2O (40 mL) was added. The resulting mixture was stirred vigorously for 20 min and the solid was filtered. The solid was washed with Et2O (2 mL×3) and dried to yield 4-(6-fluoroindolin-1-yl)-N-(4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)piperidine-1-carboxamide as a TFA salt.

Workup

  1. stirringThe resulting mixture was stirred vigorously for 20 min
  2. filtrationthe solid was filtered
  3. washThe solid was washed with Et2O (2 mL×3)
  4. customdried

Sources & evidence

ORD record
ord-9d883a3a8c28465d8906e8aee9423514
Source dataset
uspto-grants-2016_01
Patent number
US09238658B2

Reaction notes

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