HCID 178513493, compound → HCID 178513494, compound

HRID 64329Notes

Reaction equation

HRID 64329 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]2[N:14]3[N:19]=[C:18]([C:20]4[CH:25]=[CH:24][C:23]([O:26][C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)=[CH:22][CH:21]=4)[C:17]([C:33]([NH2:35])=[O:34])=[C:15]3[NH:16][C:10]=2[CH2:9]1)C1C=CC=CC=1>CO.[Pd]>[O:26]([C:23]1[CH:22]=[CH:21][C:20]([C:18]2[C:17]([C:33]([NH2:35])=[O:34])=[C:15]3[NH:16][C:10]4[CH2:9][NH:8][CH2:13][CH2:12][C:11]=4[N:14]3[N:19]=2)=[CH:25][CH:24]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 1

HCID 178513493HCID 178513493, compound

Product 1

HCID 178513494HCID 178513494, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 6-benzyl-2-(4-phenoxyphenyl)-5,6,7,8-tetrahydro-4H-pyrazolo[1′,5′:1,2]imidazo[4,5-c]pyridine-3-carboxamide (640 mg, 0.00138 mol) and 10% w/w Pd/C (700 mg) in 60 mL of MeOH was stirred at RT under 1 atm of H2 overnight. TLC and LCMS analysis showed starting material was consumed. The reaction was filtered, filtrate was concentrated to get 397 mg (77%) of 2-(4-phenoxyphenyl)-5,6,7,8-tetrahydro-4H-pyrazolo[1′,5′:1,2]imidazo[4,5-c]pyridine-3-carboxamide. 1H NMR (400 MHz, CD3OD-d4) δ 7.65-7.55 (m, 2H), 7.43-7.33 (m, 2H), 7.18-7.12 (m, 1H), 7.11-6.99 (m, 4H), 4.18 (s, 2H), 3.44 (t, J=5.8 Hz, 2H), 3.01 (t, J=5.8 Hz, 2H). MS (ESI) m/e [M+1]+ 373.9.

Workup

  1. customwas consumed
  2. filtrationThe reaction was filtered
  3. concentrationfiltrate was concentrated

Sources & evidence

ORD record
ord-4d8d1ff9d7294d32b91ae1dd12a1af08
Source dataset
uspto-grants-2016_09
Patent number
US09447106B2

Reaction notes

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