Benzoyl chloride → HCID 59507215, compound

HRID 1400115Notes

Reaction equation

HRID 1400115 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]4[C:19](=[O:20])[N:18]([CH2:21][CH2:22][C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=5)[C:17](=[O:29])[C:15]4=3)[N:10]([CH2:30][C:31]3[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[C:46](Cl)(=[O:53])[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1>ClCCl>[CH3:38][O:37][C:34]1[CH:33]=[CH:32][C:31]([CH2:30][N:10]2[C:11]3=[N:12][CH:13]=[C:14]4[C:19](=[O:20])[N:18]([CH2:21][CH2:22][C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=5)[C:17](=[O:29])[C:15]4=[C:16]3[C:8]([C:4]3[CH:3]=[C:2]([NH:1][C:46](=[O:53])[C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)[CH:7]=[CH:6][CH:5]=3)=[N:9]2)=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 59507160HCID 59507160, compound

Product 1

HCID 59507215HCID 59507215, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice cooled solution of 1-(3-aminophenyl)-3-(4-methoxybenzyl)-7-phenethylpyrazolo[3,4-b]pyrrolo[3,4-d]pyridine-6,8(3H,7H)-dione (200 mg) in dichloromethane (6 ml), triethylamine (0.08 ml, 0.59 mmol) and Benzoyl chloride (0.05 ml, 0.59 mmol) were added. The reaction mixture was warmed to room temperature and stirred for 2-3 hours. After completion of reaction (TLC, LCMS), the reaction mixture was diluted with dichloromethane (15 ml) and was washed with water (10 ml). The dichloromethane layer was dried over sodium sulfate and evaporated under reduced pressure. The crude compound was purified by reverse phase HPLC on a C-18 column to give N-(3-(3-(4-methoxybenzyl)-6,8-dioxo-7-phenethyl-3,6,7,8-tetrahydropyrazolo[3,4-b]pyrrolo[3,4-d]pyridin-1-yl)phenyl)benzamide (22 mg, 11%) as a solid.

Workup

  1. customAfter completion of reaction (TLC, LCMS)
  2. washwas washed with water (10 ml)
  3. dry with materialThe dichloromethane layer was dried over sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe crude compound was purified by reverse phase HPLC on a C-18 column

Sources & evidence

ORD record
ord-914c526883cc4c67976dd013334ba04c
Source dataset
uspto-grants-2014_12
Patent number
US08906928B2

Reaction notes

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