Potassium Sodium Tartrate → HCID 59631955, compound

HRID 2369063Notes

Reaction equation

HRID 2369063 reaction equation
CC(C[AlH]CC(C)C)C.[Cl:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N:17]1[C:21]([C:22]2[S:23][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([S:33]([CH3:36])(=[O:35])=[O:34])[CH:28]=3)=[CH:25][CH:26]=2)=[CH:20][C:19]([C:37]([CH3:41])([CH3:40])[C:38]#[N:39])=[N:18]1.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C(Cl)Cl>[Cl:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N:17]1[C:21]([C:22]2[S:23][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([S:33]([CH3:36])(=[O:34])=[O:35])[CH:28]=3)=[CH:25][CH:26]=2)=[CH:20][C:19]([C:37]([CH3:41])([CH3:40])[CH2:38][NH2:39])=[N:18]1

Participants

5

Reactant 3

HCID 9357Potassium Sodium TartrateHCID 14487Diisobutylaluminum hydrideHCID 59632347HCID 59632347, compound

Product 1

HCID 59631955HCID 59631955, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

DIBAL-H (1.0M in hexanes, 1.5 mL, 1.5 mmol) was added dropwise at −78° C. to a stirred solution of 2-[1-(2-chlorophenyl)-5-{5-[3-(methylsulfonyl)phenyl]-2-thienyl}-1H-pyrazol-3-yl]-2-methyl propanenitrile (210 mg, 0.436 mmol) in dry DCM (10 mL) under N2, the resulting mixture was stirred at −78° C. for 3 h. At −78° C. 10% aqueous Rochelle's salt solution was added dropwise to quench the reaction, the mixture was allowed to warm to rt, and extracted with DCM. The combined extracts were washed with brine, dried over Na2SO4, and evaporated in vacuo. The crude product was purified by flash chromatography (0-60% 20% MeOH/DCM) to give the title compound as a white solid (160 mg, 76%). 1HNMR (CDCl3): δ 8.04 (m, 1H), 7.83-7.80 (m, 1H), 7.74-7.71 (m, 1H), 7.57-7.42 (m, 5H), 7.20 (d, 1H), 6.71 (d, 1H), 6.52 (s, 1H0, 3.07 (s, 3H), 2.90 (s, 2H), 2.17 (brs, 2H), 1.39 (s, 6H). MS(ES): 486 [M+H]+.

Workup

  1. customAt −78° C
  2. customto quench
  3. customthe reaction
  4. temperatureto warm to rt
  5. extractionextracted with DCM
  6. washThe combined extracts were washed with brine
  7. dry with materialdried over Na2SO4
  8. customevaporated in vacuo
  9. customThe crude product was purified by flash chromatography (0-60% 20% MeOH/DCM)

Sources & evidence

ORD record
ord-f107fe68119047009ac40d91345d4ff3
Source dataset
uspto-grants-2014_04
Patent number
US08703805B2

Reaction notes

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