HCID 66617674, compound → HCID 66617707, compound

HRID 2403455Notes

Reaction equation

HRID 2403455 reaction equation
[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][N:8]([CH2:11][C:12]2[S:20][C:19]3[C:18]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)=[N:17][C:16]([C:27]4[CH:32]=[CH:31][C:30]([NH2:33])=[C:29]([N+:34]([O-])=O)[CH:28]=4)=[N:15][C:14]=3[CH:13]=2)[CH2:7][CH2:6]1)(=[O:4])=[O:3]>[Pd].CO.C(Cl)Cl>[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][N:8]([CH2:11][C:12]2[S:20][C:19]3[C:18]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)=[N:17][C:16]([C:27]4[CH:28]=[C:29]([NH2:34])[C:30]([NH2:33])=[CH:31][CH:32]=4)=[N:15][C:14]=3[CH:13]=2)[CH2:7][CH2:6]1)(=[O:4])=[O:3]

Participants

5

Reactant 1

HCID 66617674HCID 66617674, compound

Product 1

HCID 66617707HCID 66617707, compoundYield 52.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

4-[6-(4-Methanesulfonyl-piperazin-1-ylmethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-2-yl]-2-nitro-phenylamine (200 mg) was stirred under hydrogen balloon with palladium on carbon (10%, 70 mg) in a mixture of MeOH and DCM (1:1, 10 ml) at room temperature overnight. The reaction mixture was then filtered through Celite®, volatiles removed in vacuo, and the residue purified by flash chromatography to give 4-[6-(4-methanesulfonyl-piperazin-1-ylmethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-2-yl]-benzene-1,2-diamine (99 mg).

Workup

  1. filtrationThe reaction mixture was then filtered through Celite®
  2. customvolatiles removed in vacuo
  3. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-542b6583ffd74482af963be935b88e09
Source dataset
uspto-grants-2014_08
Patent number
US08802670B2

Reaction notes

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