HCID 25018483, compound → HCID 25018486, compound

HRID 1663462Notes

Reaction equation

HRID 1663462 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([S:10]([C:13]2[S:17][C:16]([NH:18][C:19]3[CH:24]=[C:23]([C:25]#[C:26][CH2:27][O:28][CH3:29])[N:22]=[C:21]([CH3:30])[N:20]=3)=[N:15][CH:14]=2)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)[CH3:2]>C1COCC1.CCOC(C)=O.[Pd]>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([S:10]([C:13]2[S:17][C:16]([NH:18][C:19]3[CH:24]=[C:23]([CH2:25][CH2:26][CH2:27][O:28][CH3:29])[N:22]=[C:21]([CH3:30])[N:20]=3)=[N:15][CH:14]=2)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)[CH3:2]

Participants

5

Reactant 1

HCID 25018483HCID 25018483, compound

Product 1

HCID 25018486HCID 25018486, compoundYield 93%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of [5-(3-Ethoxy-benzenesulfonyl)-thiazol-2-yl]-[6-(3-methoxy-prop-1-ynyl)-2-methyl-pyrimidin-4-yl]-amine (32.0 mg, 0.072 mol) and Pd—C (10%, 2.0 mg) in THF (1.00 mL) and EtOAc (1.00 mL) was stirred under H2 (70 psi, Parr) for 30 min. The reaction mixture was filtered through Celite using EtOAc (ca. 50 mL). The filtrate concentrated under reduced pressure to give the title compound (30 mg, 93%) as an off-white solid. LCMS (m/z): 449 (M+H)+

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationThe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-6d84e1df399a4b81a8a698e7de772d5f
Source dataset
uspto-grants-2011_10
Patent number
US08034954B2

Reaction notes

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