HCID 11994313, compound → N-{5-[Methoxy(phenyl)acetyl]-1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazol-3-yl}-4-(4-methylpiperazin-1-yl)benzene-1-carboximidic acid

HRID 729242Notes

Reaction equation

HRID 729242 reaction equation
[CH3:1][O:2][C@H:3]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:4]([N:6]1[CH2:13][C:12]2[C:11]([NH:14][C:15](=[O:29])[C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]4)=[CH:18][CH:17]=3)=[N:10][N:9](C(OCC)=O)[C:8]=2[CH2:7]1)=[O:5]>CO.C(N(CC)CC)C>[CH3:1][O:2][C@H:3]([C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[C:4]([N:6]1[CH2:13][C:12]2[C:11]([NH:14][C:15](=[O:29])[C:16]3[CH:17]=[CH:18][C:19]([N:22]4[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]4)=[CH:20][CH:21]=3)=[N:10][NH:9][C:8]=2[CH2:7]1)=[O:5]

Participants

4

Reactant 1

HCID 11994313HCID 11994313, compound

Product 1

HCID 11442891N-{5-[Methoxy(phenyl)acetyl]-1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazol-3-yl}-4-(4-methylpiperazin-1-yl)benzene-1-carboximidic acidYield 46.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8471TriethylamineSolvent

Procedure

A solution of ethyl 5-[(2R)-2-methoxy-2-phenylethanoyl]-3-{[4-(4-methylpiperazin-1-yl)benzoyl]amino}-5,6-dihydropyrrolo[3,4-c]pyrazole-1(4H)-carboxylate (3.94 g, 7.2 mmol) in methanol (MeOH, 130 ml) and triethylamine (Et3N, 13 ml) was stirred at room temperature for 16 hours (some precipitation occurred). The solid was separated and washed with Et2O, to give 1.6 g of the title compound. Solution was evaporated up to few milliliters, and a second fraction of solid product was separated (1.62 g). The two fractions were joined and analyzed by LC-MS (purity around 90% 254 and 220 nM). After chromatographic purification (short silica gel column, DCM/MeOH 45:5) 2.83 g (83%) of the title compound were obtained as a white solid. M.p 289° C.; [M+H]+ 475;

Workup

  1. customsome precipitation
  2. customThe solid was separated
  3. washwashed with Et2O

Sources & evidence

ORD record
ord-1b031b364ce04fb6be8dadce67a60bba
Source dataset
uspto-grants-2009_09
Patent number
US07582628B2

Reaction notes

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