Sodium → HCID 50991860, compound

HRID 220403Notes

Reaction equation

HRID 220403 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-18ebe9a8ffc2443fbf5d1ee0b9ba2330
Source dataset
uspto-grants-2012_06
Patent number
US08202881B2

Reaction notes

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