Dimethylformamide → Ammonia

HRID 1639616Notes

Reaction equation

HRID 1639616 reaction equation
[CH3:1][O:2][C:3]1[C:17]([O:18][CH3:19])=[CH:16][C:6]2[NH:7][C:8]([C:10]3[C:14]([NH2:15])=[CH:13][NH:12][N:11]=3)=[N:9][C:5]=2[CH:4]=1.CN(C(ON1N=NC2C=[CH:32][CH:33]=[CH:34][C:29]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[OH-:42].[Na+].[CH3:44][N:45]([CH:47]=O)[CH3:46]>>[NH3:7].[CH3:19][O:18][C:17]1[C:3]([O:2][CH3:1])=[CH:4][C:5]2[NH:9][C:8]([C:10]3[C:14]([NH:15][C:32]([CH:33]4[CH2:34][CH2:29][CH2:46][N:45]([CH3:44])[CH2:47]4)=[O:42])=[CH:13][NH:12][N:11]=3)=[N:7][C:6]=2[CH:16]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178486794HCID 178486794, compound

Product 2

HCID 222AmmoniaHCID 178486786HCID 178486786, compound

Procedure

To a solution of 3-(5,6-dimethoxy-1H-benzimidazol-2-yl)-1H-pyrazol-4-ylamine (65 mg, 0.25 mmol) (Example 15B) (rac)-1-methyl-piperidine-3-carboxylic acid-hydrocholoride salt (50 mg, 0.27 mmol) and disopropylethylamine (50%, 0.27 mmol) in DMF (1 ml) was added TBTU (97 mg, 0.30 mmol). The mixture was stirred at room temperature for approximately 16 hours after which 1N aqueous NaOH (1 ml) was added and the mixture stirred for a further 1 hours. The mixture was then evaporated to dryness in vacuo and the residue purified by flash column chromatography (SiO2, eluting with a gradient of DCM:MeOH (98:2) to DCM:MeOH; conc. Aq. NH3 (70:30:3) to give N-[3-(5,6-dimethoxy-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-rac-1-methyl-piperidine 3-carboxamide (20 mg) as a colourless gum (LC/MS (basic method): Rt 2.35 min, (M+H)+ 385).

Workup

  1. additionwas added
  2. customThe mixture was then evaporated to dryness in vacuo
  3. customthe residue purified by flash column chromatography (SiO2
  4. washeluting with a gradient of DCM:MeOH (98:2) to DCM

Sources & evidence

ORD record
ord-190f6e8a5349405ea6d0e784462e2e18
Source dataset
uspto-grants-2012_02
Patent number
US08110573B2

Reaction notes

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