Triethylamine → HCID 20616897, compound

HRID 2119592Notes

Reaction equation

HRID 2119592 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]1[S:8][C:9]([C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:13])=[CH:10][N:11]=1.[C:20](Cl)(=[O:25])[CH2:21][CH2:22][CH2:23][CH3:24].CCN(CC)CC>CO.C(Cl)Cl>[C:12]([C:9]1[S:8][C:7]([NH:6][CH2:5][CH2:4][CH2:3][NH:2][C:20](=[O:25])[CH2:21][CH2:22][CH2:23][CH3:24])=[N:11][CH:10]=1)(=[O:13])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 61186Valeryl chlorideHCID 23442764HCID 23442764, compound

Product 1

HCID 20616897HCID 20616897, compoundYield 43.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 11.9 mg (0.04 mmol) [2-(3-Amino-propylamino)-thiazol-5-yl]-phenyl-methanone hydrochloride, 5.8 mg (0.048 mmol) pentanoyl chloride and 39 ul (0.28 mmol) NEt3 in 1 ml methanol and 0.5 ml DCM was stirred at room temperature for 16 h. After evaporation to dryness the residue was taken up in 1.5 ml MeOH/formic acid 1/1 and subjected to preparative HPLC separation on reversed phase eluting with an acetonitrile/water gradient. Evaporation of product fractions yielded 6 mg (43%) of the title compound.

Workup

  1. customAfter evaporation to dryness the residue
  2. customHPLC separation on reversed phase
  3. washeluting with an acetonitrile/water gradient
  4. customEvaporation of product fractions

Sources & evidence

ORD record
ord-afd821e67fc54e32851a96194651bc59
Source dataset
uspto-grants-2004_02
Patent number
US06686381B2

Reaction notes

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