Triethylamine → HCID 20801105, compound

HRID 1071684Notes

Reaction equation

HRID 1071684 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]2[O:11][N:10]=[C:9]([CH2:12][N:13]3[C:21]4[C:16](=[CH:17][C:18]([C:22](O)=[O:23])=[CH:19][CH:20]=4)[CH:15]=[C:14]3[C:25](=[O:36])[NH:26][CH:27]3[CH2:32][CH2:31][N:30]([CH:33]([CH3:35])[CH3:34])[CH2:29][CH2:28]3)[CH:8]=2)=[CH:4][CH:3]=1.CCN(CC)CC>C1COCC1.ClC(OCC)=O>[CH:33]([N:30]1[CH2:31][CH2:32][CH:27]([NH:26][C:25]([C:14]2[N:13]([CH2:12][C:9]3[CH:8]=[C:7]([C:5]4[S:6][C:2]([Cl:1])=[CH:3][CH:4]=4)[O:11][N:10]=3)[C:21]3[C:16]([CH:15]=2)=[CH:17][C:18]([CH2:22][OH:23])=[CH:19][CH:20]=3)=[O:36])[CH2:28][CH2:29]1)([CH3:35])[CH3:34]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 22394458HCID 22394458, compound

Product 1

HCID 20801105HCID 20801105, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 10928Ethyl chloroformateSolvent

Conditions

Temperature
-7 °C

Procedure

To a solution of 100 mg 1-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-2-(1-isopropyl-piperidin-4-ylcarbamoyl)-1H-indole-5-carboxylic acid and 50 μl NEt3 in 4 ml THF, 17 μl ethyl chloroformate were added at −7° C. After stirring for 2 h at −7° C. the reaction mixture was filtered, the filtrate was treated with 24 mg NaBH4 and warmed to room temperature. After 2 h additional 24 mg NaBH4 were added and the reaction mixture stirred for 16 h. Then, 110 μl MeOH in 4 ml THF were added within 2 h and the reaction mixture was stirred for additional 4 h at room temperature. After removal of the solvents under reduced pressure the residue was purified by chromatography on silica gel eluting with DCM/MeOH 8:2. The fractions containing the product were collected and evaporated under reduced pressure.

Workup

  1. filtrationwas filtered
  2. additionthe filtrate was treated with 24 mg NaBH4
  3. temperaturewarmed to room temperature
  4. additionAfter 2 h additional 24 mg NaBH4 were added
  5. stirringthe reaction mixture stirred for 16 h
  6. additionThen, 110 μl MeOH in 4 ml THF were added within 2 h
  7. stirringthe reaction mixture was stirred for additional 4 h at room temperature
  8. customAfter removal of the solvents under reduced pressure the residue
  9. customwas purified by chromatography on silica gel eluting with DCM/MeOH 8:2
  10. additionThe fractions containing the product
  11. customwere collected
  12. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-178d00d386e44523a913ee65e9300e6a
Source dataset
uspto-grants-2005_06
Patent number
US06906084B2

Reaction notes

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