Diisopropylethylamine → HCID 10288343, compound

HRID 2416204Notes

Reaction equation

HRID 2416204 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][C:12]2[S:13][CH:14]=[C:15]([C:17]3[C:18](=[O:31])[NH:19][C:20]4[C:25]([CH:26]=3)=[CH:24][CH:23]=[C:22]([C:27]([F:30])([F:29])[F:28])[CH:21]=4)[N:16]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C>CN(C=O)C.[Pd]>[C:5]1([S:8]([CH2:11][C:12]2[S:13][CH:14]=[C:15]([C:17]3[C:18](=[O:31])[NH:19][C:20]4[C:25]([CH:26]=3)=[CH:24][CH:23]=[C:22]([C:27]([F:30])([F:29])[F:28])[CH:21]=4)[N:16]=2)(=[O:10])=[O:9])[CH:4]=[CH:3][CH:2]=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 81531DiisopropylethylamineHCID 10152113HCID 10152113, compound

Product 1

HCID 10288343HCID 10288343, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-[2-(4-chloro-benzenesulfonylmethyl)-thiazol-4-yl]-7-trifluoromethyl-1H-quinolin-2-one (Example 103, 67 mg, 0.14 mmol), 0.5 mL of IPEA, and 0.1 g of Pd-C (10%) in anhydrous DMF (10 mL) was stirred under H2 overnight. The catalysts were filtered through Celite and the filtrate was concentrated. CH2Cl2 was added and precipitates were filtered, washed with MeOH, CH2Cl2 to afford the title compound as a tan solid. MS m/z: 451.2 (M+1).

Workup

  1. filtrationThe catalysts were filtered through Celite
  2. concentrationthe filtrate was concentrated
  3. additionCH2Cl2 was added
  4. customprecipitates
  5. filtrationwere filtered
  6. washwashed with MeOH, CH2Cl2

Sources & evidence

ORD record
ord-fc88dd88748d4420b6a34959fc780c06
Source dataset
uspto-grants-2004_11
Patent number
US06822097B1

Reaction notes

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