Formaldehyde → HCID 24816293, compound

HRID 28906Notes

Reaction equation

HRID 28906 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:6]=[C:7]([C:11]2[NH:40][C:14]3=[N:15][CH:16]=[CH:17][C:18]([C:19]4[C:20]([C:28]5[CH:33]=[CH:32][C:31]([NH:34][C:35](=[O:39])[N:36]([CH3:38])[CH3:37])=[CH:30][CH:29]=5)=[N:21][N:22]([CH2:24][CH2:25][NH:26][CH3:27])[CH:23]=4)=[C:13]3[CH:12]=2)[CH:8]=[CH:9][CH:10]=1)[CH3:3].[OH-].[Na+].[CH2:43]=O.O>CO.[OH-].[OH-].[Pd+2]>[CH3:27][N:26]([CH3:43])[CH2:25][CH2:24][N:22]1[CH:23]=[C:19]([C:18]2[CH:17]=[CH:16][N:15]=[C:14]3[NH:40][C:11]([C:7]4[CH:8]=[CH:9][CH:10]=[C:5]([CH2:4][N:2]([CH3:3])[CH3:1])[CH:6]=4)=[CH:12][C:13]=23)[C:20]([C:28]2[CH:29]=[CH:30][C:31]([NH:34][C:35](=[O:39])[N:36]([CH3:38])[CH3:37])=[CH:32][CH:33]=2)=[N:21]1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 962WaterHCID 14798Sodium HydroxideHCID 24816291HCID 24816291, compound

Product 1

HCID 24816293HCID 24816293, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 9942167Palladium hydroxideSolvent

Procedure

To N′-(4-{4-(2-{3-[(dimethylamino)methyl]phenyl}-1H-pyrrolo[2,3-b]pyridin-4-yl)-1-[2-(methylamino)ethyl]-1H-pyrazol-3-yl}phenyl)-N,N-dimethylurea.3TFA (300 mg, 0.34 mMol) in MeOH (10 mL) was added with stirring at RT aq. 1 N NaOH (1.1 mL, 1.1 mMol), 37 wt. % CH2O in water (50 uL, 0.67 mMol) and 20% Pd(OH)2/C (Pearlman's catalyst) (˜10 mg). A balloon of H2 was attached and the reaction stirred at RT for 3 days. The reaction was evaporated to dryness under vacuum, taken up in (9:1) CHCl3/iPrOH (15 mL) and treated with excess methyl isatoic anhydride polystyrene resin (˜500 mg, >1.8 mMol/g). After stirring at RT for 4 h the reaction was filtered, rinsed with (9:1) CHCl3/iPrOH, and the filtrate concentrated to dryness under vacuum. Purification by Gilson HPLC provided the title compound (56.6 mg, 30%) as a white solid. ESMS [M+H]+: 551.6

Workup

  1. customThe reaction was evaporated to dryness under vacuum
  2. additiontreated with excess methyl isatoic anhydride polystyrene resin (˜500 mg, >1.8 mMol/g)
  3. stirringAfter stirring at RT for 4 h the reaction
  4. filtrationwas filtered
  5. washrinsed with (9:1) CHCl3/iPrOH
  6. concentrationthe filtrate concentrated to dryness under vacuum
  7. customPurification by Gilson HPLC

Sources & evidence

ORD record
ord-a21cb599a8e54e0d8926179799c9582e
Source dataset
uspto-grants-2008_09
Patent number
US07419988B2

Reaction notes

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