HCID 86712632, compound → HCID 86712635, compound

HRID 1778963Notes

Reaction equation

HRID 1778963 reaction equation
[CH3:1][O:2][C:3](=[O:40])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]#[C:12][C:13]1[C:18]([CH3:19])=[CH:17][N:16]=[C:15]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([N:27]3[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:29][CH2:28]3)=[CH:23][CH:22]=2)[N:14]=1>CN(C=O)C.CCOC(C)=O.[Pd]>[CH3:1][O:2][C:3](=[O:40])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][CH2:12][C:13]1[C:18]([CH3:19])=[CH:17][N:16]=[C:15]([NH:20][C:21]2[CH:22]=[CH:23][C:24]([N:27]3[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:37])([CH3:38])[CH3:39])=[O:34])[CH2:29][CH2:28]3)=[CH:25][CH:26]=2)[N:14]=1

Participants

5

Reactant 1

HCID 86712632HCID 86712632, compound

Product 1

HCID 86712635HCID 86712635, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 4-(4-((4-((2-(2-methoxy-2-oxoethyl)phenyl)ethynyl)-5-methylpyrimidin-2-yl)amino)phenyl)piperazine-1-carboxylate (A7) (60 mg, 0.11 mmol) in anhydrous DMF (10 mL) was added a slurry of 10% Pd/C (30 mg) in DMF (2 mL). The resulting mixture was stirred at room temperature under an atmosphere of hydrogen for 72 hours then diluted with EtOAc (30 mL) and filtered through a plug of Celite, washing with EtOAc (50 mL). The filtrate was evaporated to dryness to give the title compound A8 as a brown oily residue (44 mg, 73%); 1H NMR (400 MHz, CDCl3) δ 8.06 (s, 1H), 7.52 (dt, J=8.0, 2.5 Hz, 2H), 7.25-7.17 (m, 4H), 6.92 (dd, J=7.2, 5.1 Hz, 2H), 6.88 (s, 1H), 3.72 (s, 2H), 3.68 (d, J=3.0 Hz, 3H), 3.61-3.56 (m, 4H), 3.07 (dd, J=9.3, 5.1 Hz, 6H), 2.06 (s, 3H), 1.48 (s, 9H). LC-MS-A: rt 6.260 min; m/z 546.2 [M+H]+.

Workup

  1. filtrationfiltered through a plug of Celite
  2. washwashing with EtOAc (50 mL)
  3. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-12e978437e5f4ddd9c158bdb49d4ffc1
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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