Water → Trifluoroacetic acid

HRID 513209Notes

Reaction equation

HRID 513209 reaction equation
C(OC([N:8]1[C:12]2=[C:13]([Cl:17])[N:14]=[CH:15][CH:16]=[C:11]2[C:10]([CH2:18][CH2:19][O:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][C:28]([F:31])([F:30])[F:29])=[CH:23][CH:22]=2)=[C:9]1[C:32]([OH:34])=[O:33])=O)(C)(C)C.O.CSC.[C:39]([OH:45])([C:41]([F:44])([F:43])[F:42])=[O:40]>C(Cl)Cl>[Cl:17][C:13]1[N:14]=[CH:15][CH:16]=[C:11]2[C:10]([CH2:18][CH2:19][O:20][C:21]3[CH:22]=[CH:23][C:24]([O:27][C:28]([F:30])([F:29])[F:31])=[CH:25][CH:26]=3)=[C:9]([C:32]([OH:34])=[O:33])[NH:8][C:12]=12.[C:39]([OH:45])([C:41]([F:44])([F:43])[F:42])=[O:40]

Participants

7

Reactant 4

HCID 962WaterHCID 1068Dimethyl SulfideHCID 6422Trifluoroacetic acidHCID 86720580HCID 86720580, compound

Product 2

HCID 6422Trifluoroacetic acidYield 360%HCID 71487648HCID 71487648, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(tert-butoxycarbonyl)-7-chloro-3-{2-[4-(trifluoromethoxy)phenoxy]ethyl}-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (9.4 mg, 0.019 mmol) in DCM (0.5 mL) was added water (0.01 mL), dimethylsulfide (0.01 mL), and then TFA (0.5 mL, 6.5 mmol). Upon complete consumption of starting material, the mixture was concentrated in vacuo to yield the title compound as a TFA salt (7.8 mg). HRMS (ESI) calc (M+H)+=401.0510. found 401.0509.

Workup

  1. customUpon complete consumption of starting material
  2. concentrationthe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-11e2c6f7759d4a289b304d5483c1b515
Source dataset
uspto-grants-2015_08
Patent number
US09102673B2

Reaction notes

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