Sodium → HCID 50991860, compound

HRID 1188081Notes

Reaction equation

HRID 1188081 reaction equation
[Na].[CH:2]1([N:5]([CH:33]2[CH2:35][CH2:34]2)[C:6]([C:8]2[N:30]([CH2:31][CH3:32])[C:11]3=[N:12][C:13]([NH:20][C:21]4[CH:25]=[C:24]([CH:26]=[O:27])[N:23]([CH2:28][CH3:29])[N:22]=4)=[C:14]4[N:18]=[CH:17][N:16]([CH3:19])[C:15]4=[C:10]3[CH:9]=2)=[O:7])[CH2:4][CH2:3]1>CO>[CH:33]1([N:5]([CH:2]2[CH2:3][CH2:4]2)[C:6]([C:8]2[N:30]([CH2:31][CH3:32])[C:11]3=[N:12][C:13]([NH:20][C:21]4[CH:25]=[C:24]([CH2:26][OH:27])[N:23]([CH2:28][CH3:29])[N:22]=4)=[C:14]4[N:18]=[CH:17][N:16]([CH3:19])[C:15]4=[C:10]3[CH:9]=2)=[O:7])[CH2:34][CH2:35]1

Participants

4

Reactant 2

HCID 5360545SodiumHCID 50991859HCID 50991859, compound

Product 1

HCID 50991860HCID 50991860, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium boronhydride (10 wt % on alumina, 13.14 mg, 0.035 mmol) was added to N,N-dicyclopropyl-6-ethyl-4-(1-ethyl-5-formyl-1H-pyrazol-3-ylamino)-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide (example 101C, 16 mg, 0.035 mmol) in methanol (1 mL) at room temperature and the reaction mixture stirred for 0.5 h. The solid alumina was filtered off and the filtrate was concentrated in vacuo. The crude product was purified by flash chromatography on silica gel using an automated ISCO system (4 g column, eluting with 2-10% methanol/dichloromethane). N,N-dicyclopropyl-6-ethyl-4-(1-ethyl-5-(hydroxymethyl)-1H-pyrazol-3-ylamino)-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide (14 mg, 86% yield) was obtained as a white solid.

Workup

  1. filtrationThe solid alumina was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe crude product was purified by flash chromatography on silica gel using
  4. washan automated ISCO system (4 g column, eluting with 2-10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-fb20e5a8e6994e5cba145255ecb9f5c9
Source dataset
uspto-grants-2014_03
Patent number
US08673933B2

Reaction notes

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