Ammonium Hydroxide → HCID 22318542, compound

HRID 497433Notes

Reaction equation

HRID 497433 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]3[C:14](=[O:37])[N:15]([C:18]4[CH:23]=[CH:22][C:21]([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=5[CH2:30][N:31]([CH3:36])[C:32]([NH:34][CH3:35])=[O:33])=[CH:20][CH:19]=4)[CH2:16][CH2:17][C:12]=3[C:11]([C:38](OCC)=[O:39])=[N:10]2)=[CH:5][CH:4]=1.[NH4+:43].[OH-]>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]3[C:14](=[O:37])[N:15]([C:18]4[CH:23]=[CH:22][C:21]([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=5[CH2:30][N:31]([CH3:36])[C:32]([NH:34][CH3:35])=[O:33])=[CH:20][CH:19]=4)[CH2:16][CH2:17][C:12]=3[C:11]([C:38]([NH2:43])=[O:39])=[N:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 22318560HCID 22318560, compound

Product 1

HCID 22318542HCID 22318542, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Ethyl 1-(4-methoxyphenyl)-6-[2′-({methyl[(methylamino)carbonyl]amino}methyl)-1,1′-biphenyl-4-yl]-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylate (130 mg, 0.2 mmol) was dissolved in 7.5 mL of 1,4-dioxane. Concentrated NH4OH (7.5 mL) was added. The reaction vessel was sealed and the mixture was stirred at room temperature for 4 days. The mixture was stripped and chromatographed using 3% MeOH:CHCl3 with 0.1% concentrated NH4OH. The fractions containing desired product were combined and purified by reverse phase HPLC (C18 reverse phase column, eluted with a H2O/CH3CN gradient with 0.05% TFA) to give 71 mg of desired product (48% yield). MS (ES+): 539.4, (M+H)+. 1HNMR (CDCl3) δ 7.48 (t, 2H), 7.39-7.19 (m, 9H), 6.95 (m, 3H), 6.00 (bs, 1H), 4.47 (s, 2H), 4.189 (t, 2H), 3.83 (s, 3H), 3.41 (t, 2H), 2.77 (s, 3H), 2.72 (s, 3H) ppm.

Workup

  1. customThe reaction vessel was sealed
  2. customchromatographed
  3. additionThe fractions containing desired product
  4. custompurified by reverse phase HPLC (C18 reverse phase column
  5. washeluted with a H2O/CH3CN gradient with 0.05% TFA)

Sources & evidence

ORD record
ord-53b3a1f5d6f84b94a172995a35a1c00f
Source dataset
uspto-grants-2005_09
Patent number
US06949550B2

Reaction notes

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