Formic Acid → HCID 59540634, compound

HRID 1677492Notes

Reaction equation

HRID 1677492 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][C:5]([C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([C:20]4[CH:25]=[C:24]([O:26][CH3:27])[C:23]([O:28][CH3:29])=[C:22]([O:30][CH3:31])[CH:21]=4)[N:18]=3)[NH:13][CH:12]=2)=[O:10])([CH3:8])[CH2:4][CH2:3]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:51](O)=[O:52].N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH3:8][C:5]1([C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([C:20]4[CH:21]=[C:22]([O:30][CH3:31])[C:23]([O:28][CH3:29])=[C:24]([O:26][CH3:27])[CH:25]=4)[N:18]=3)[NH:13][CH:12]=2)=[O:10])[CH2:4][CH2:3][CH:2]([O:1][CH:51]=[O:52])[CH2:7][CH2:6]1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 59540549HCID 59540549, compound

Product 1

HCID 59540634HCID 59540634, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (4-hydroxy-1-methyl-cyclohexyl)-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanone (19 mg, 0.045 mmol), triphenyl phosphine (23 mg, 0.088 mmol), and formic acid (0.003 ml, 0.087 mmol), in THF (0.4 ml), was treated with diethyl azodicarboxylate (0.01 ml, 0.092 mmol). After stirring at room temperature for 2 days, the reaction mixture was purified by preparative thin layer chromatography using 70% EtOAc in Hexanes as eluant providing 12 mg (59%) of formic acid 4-methyl-4-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbonyl]-cyclohexyl ester as a white solid. M+H=454.

Workup

  1. customthe reaction mixture was purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-29a66d1c0508440faa36329f0e2dc67f
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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