Triethylamine → HCID 46927118, compound

HRID 2188575Notes

Reaction equation

HRID 2188575 reaction equation
I[C:2]1[CH:3]=[N:4][N:5]([CH:7]2[CH2:12][CH2:11][CH:10]([N:13]3[CH2:16][CH:15]([NH:17][C:18]([CH2:20][NH:21][C:22](=[O:33])[C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=4)=[O:19])[CH2:14]3)[CH2:9][CH2:8]2)[CH:6]=1.[Si:34]([C:38]#[CH:39])([CH3:37])([CH3:36])[CH3:35].CCN(CC)CC>CN(C=O)C.[Cu]I>[F:30][C:29]([F:32])([F:31])[C:25]1[CH:24]=[C:23]([CH:28]=[CH:27][CH:26]=1)[C:22]([NH:21][CH2:20][C:18](=[O:19])[NH:17][CH:15]1[CH2:16][N:13]([CH:10]2[CH2:11][CH2:12][CH:7]([N:5]3[CH:6]=[C:2]([C:39]#[C:38][Si:34]([CH3:37])([CH3:36])[CH3:35])[CH:3]=[N:4]3)[CH2:8][CH2:9]2)[CH2:14]1)=[O:33]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 49763220HCID 49763220, compound

Product 1

HCID 46927118HCID 46927118, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of N-({1-[4-(4-Iodo-pyrazol-1-yl)-cyclohexyl]-azetidin-3-ylcarbamoyl}-methyl)-3-trifluoromethyl-benzamide (as prepared in Example 28, 120 mg, 0.20 mmol), TMS-acetylene (Fluka, 20 mg, 0.40 mmol), Pd(Cl2)dppf (Aldrich, 16 mg, 0.02 mmol), CuI (Aldrich, 3.8 mg, 0.02 mmol) and Et3N (56 uL, 0.40 mmol) in DMF (5 mL) was heated to 80° C. overnight. The reaction was purified column chromatography purification (0-100% ethyl acetate in hexanes with NH3 in MeOH) resulting in the title compound as a white solid.

Workup

  1. customThe reaction was purified
  2. customcolumn chromatography purification (0-100% ethyl acetate in hexanes with NH3 in MeOH)

Sources & evidence

ORD record
ord-20e360f02b71424890aa7add65dabb02
Source dataset
uspto-grants-2012_12
Patent number
US08324186B2

Reaction notes

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