HCID 66760496, compound → HCID 66760330, compound

HRID 389507Notes

Reaction equation

HRID 389507 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:16]2[CH:17]=[N:18][N:19]([CH:21]3[CH2:26][CH2:25][N:24]([C:27](=[O:29])[CH3:28])[CH2:23][CH2:22]3)[CH:20]=2)=[C:6]2[CH:10]=[C:9]([C:11]3[CH2:15][CH2:14][CH2:13][CH:12]=3)[O:8][C:7]=12>C1COCC1.[Pd]>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:16]2[CH:17]=[N:18][N:19]([CH:21]3[CH2:26][CH2:25][N:24]([C:27](=[O:29])[CH3:28])[CH2:23][CH2:22]3)[CH:20]=2)=[C:6]2[CH:10]=[C:9]([CH:11]3[CH2:12][CH2:13][CH2:14][CH2:15]3)[O:8][C:7]=12

Participants

4

Reactant 1

HCID 66760496HCID 66760496, compound

Product 1

HCID 66760330HCID 66760330, compoundYield 40.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

1-{4-[4-(7-Amino-2-cyclopent-1-enyl-furo[2,3-c]pyridin-4-yl)-pyrazol-1-yl]-piperidin-1-yl}-ethanone (80 mg, 0.2 mmol) and10% Pd/C (20 mg) were suspended in dry THF (30 mL) and the solution was stirred at rt under a hydrogen balloon overnight. The Pd/C was filtered and the filtrate was concentrated. The residue was purified by preparative TLC (5:1 DCM:MeOH) to afford 32 mg (40%) of the title compound. 1H NMR (400 MHz, CD3OD): δ 8.03 (d, J=0.8 Hz, 1H), 7.80-7.81 (d, J=0.8 Hz, 1H), 7.79 (s, 1H), 6.70 (s, 1H), 4.62-4.70 (m, 1H), 4.49-4.51 (m, 1H), 4.10-4.22 (m, 1H), 3.31-3.33 (m, 1H), 2.76-2.85 (m, 1H), 2.15-2.20 (m, 2H), 2.14 (s, 3H), 2.08-2.14 (m, 2H), 1.92-2.08 (m, 2H), 1.85-1.88 (m, 5H), 1.70-1.78 (m, 2H); MS (ESI): 394.16 [M+H]+; HPLC tR=2.40 min (ZQ3: polar—4 min).

Workup

  1. filtrationThe Pd/C was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by preparative TLC (5:1 DCM:MeOH)

Sources & evidence

ORD record
ord-4fd76c934934436d8a6e9a9d914955d3
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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