HCID 53374178, compound → HCID 67409073, compound

HRID 869699Notes

Reaction equation

HRID 869699 reaction equation
[C:1]1([C:6]2[CH:11]=[C:10]([NH:12][CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[N:9]3[N:19]=[C:20]([C:22]4[C:31]([CH3:32])=[N:30][C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[N:23]=4)[CH:21]=[C:8]3[N:7]=2)[CH2:5][CH2:4][CH2:3][CH:2]=1>[Pd].ClCCl.CO>[CH:1]1([C:6]2[CH:11]=[C:10]([NH:12][CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[N:9]3[N:19]=[C:20]([C:22]4[C:31]([CH3:32])=[N:30][C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[N:23]=4)[CH:21]=[C:8]3[N:7]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 1

HCID 53374178HCID 53374178, compound

Product 1

HCID 67409073HCID 67409073, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of 5-cyclopent-1-en-1-yl-2-(3-methylquinoxalin-2-yl)-N-(tetrahydro-2H-pyran-4-yl)pyrazolo[1,5-a]pyrimidin-7-amine (30 mg, 0.0703 mmol) and palladium on carbon (5%, 30 mg) in dichloromethane (2.0 mL) and methanol (2.0 mL) was stirred for 3 h under hydrogen atmosphere. Then reaction mixture was filtrated with chloroform, and the filtrate was concentrated in vacuo. The crude was purified by silica gel column chromatography (hexane:ethyl acetate=19:1 to 1:1) to give 5-cyclopentyl-2-(3-methylquinoxalin-2-yl)-N-(tetrahydro-2H-pyran-4-yl)pyrazolo[1,5-a]pyrimidin-7-amine (the compound of Example 1.012 listed in the Table of Examples as described hereinafter). 1H-NMR (400 MHz, CDCl3): δ 1.67-1.95 (8H, m), 2.08-2.20 (4H, m), 3.05 (3H, s), 3.11-3.23 (1H, m), 3.60 (2H, ddd, J=11.8, 11.8, 2.4 Hz), 3.74-3.85 (1H, m), 4.10 (2H, ddd, J=11.5, 3.3, 3.3 Hz), 5.94 (1H, s), 6.32 (1H, d, J=7.9 Hz), 7.02 (1H, s), 7.71-7.79 (2H, m), 8.04-8.08 (1H, m), 8.16-8.20 (1H, m).

Workup

  1. customThen reaction mixture
  2. filtrationwas filtrated with chloroform
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe crude was purified by silica gel column chromatography (hexane:ethyl acetate=19:1 to 1:1)

Sources & evidence

ORD record
ord-df1e6eb563f643728f7fe4c018552e27
Source dataset
uspto-grants-2015_03
Patent number
US08969376B2

Reaction notes

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