HCID 123573018, compound → HCID 118161582, compound

HRID 2203686Notes

Reaction equation

HRID 2203686 reaction equation
[Si]([O:18][CH:19]1[CH2:24][CH:23]2[CH:21]([CH:22]2[C:25]2[N:29]([CH2:30][CH:31]3[CH2:33][CH2:32]3)[N:28]=[C:27]([C:34]3[CH:35]=[C:36]([O:41][C:42]([F:45])([F:44])[F:43])[C:37]([NH2:40])=[N:38][CH:39]=3)[CH:26]=2)[CH2:20]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1>O1CCCC1.F.F.F.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>[NH2:40][C:37]1[N:38]=[CH:39][C:34]([C:27]2[CH:26]=[C:25]([CH:22]3[CH:23]4[CH:21]3[CH2:20][CH:19]([OH:18])[CH2:24]4)[N:29]([CH2:30][CH:31]3[CH2:33][CH2:32]3)[N:28]=2)=[CH:35][C:36]=1[O:41][C:42]([F:43])([F:45])[F:44]

Participants

5

Reactant 1

HCID 123573018HCID 123573018, compound

Product 1

HCID 118161582HCID 118161582, compoundYield 75.5%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 175505N,N-Diethylethanamine trihydrofluorideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 5-(5-(3-((tert-butyldiphenylsilyl)oxy)bicyclo[3.1.0]hexan-6-yl)-1-(cyclopropylmethyl)-1H-pyrazol-3-yl)-3-(trifluoromethoxy)pyridin-2-amine (0.30 g, 0.47 mmol) in tetrahydrofuran (2 mL) and triethylamine trihydrofluoride (2 mL) was heated to 60° C. for 16 h. The reaction was diluted with saturated aqueous sodium bicarbonate, and the resulting mixture was extracted with ethyl acetate (2×10 mL). The collected organic was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and concentrated. Purification by flash column chromatography (50% ethyl acetate in petroleum ether) provided product as a solid (140 mg, 75% yield). LCMS (ESI) [MH]+=394.9.

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate (2×10 mL)
  2. washThe collected organic was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash column chromatography (50% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-ef355518e5e1459c815a301ec844e7e3
Source dataset
uspto-grants-2016_06
Patent number
US09365583B2

Reaction notes

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