Triethylamine → HCID 59771311, compound

HRID 2219014Notes

Reaction equation

HRID 2219014 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([O:27][CH2:28][CH2:29][OH:30])[CH:8]=[C:9]2[C:13]=1[NH:12][N:11]=[C:10]2[S:14]([C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1)(=[O:16])=[O:15].C(N(CC)CC)C>CN(C=O)C.O>[C:17]1([S:14]([C:10]2[C:9]3[C:13]4[N:12]([CH2:2][CH2:3][O:4][C:5]=4[CH:6]=[C:7]([O:27][CH2:28][CH2:29][OH:30])[CH:8]=3)[N:11]=2)(=[O:16])=[O:15])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 178527290HCID 178527290, compound

Product 1

HCID 59771311HCID 59771311, compoundYield 94.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2-[7-(2-chloroethoxy)-3-(naphthalene-1-sulfonyl)-1H-indazol-5-yloxy]ethanol (1.18 g, 2.65 mmoles) and triethylamine (0.4 ml, 2.65 mmoles) in DMF was stirred overnight at 70° C., cooled to room temperature, diluted with water and extracted with EtOAc. The extracts were combined, washed sequentially with water and brine, dried over Na2SO4 and concentrated under vacuum. The resultant residue was purified by flash chromatography using as eluent 5% CH3OH/EtOAc to afford the title compound (1.03 g, 2.5 mmoles), identified by HNMR and mass spectral analyses.

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with EtOAc
  3. washwashed sequentially with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum
  6. customThe resultant residue was purified by flash chromatography

Sources & evidence

ORD record
ord-520d127576584e94830b0cd8206c2c17
Source dataset
uspto-grants-2008_08
Patent number
US07414051B2

Reaction notes

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