Trimethyl orthoformate → HCID 136060816, compound

HRID 1851433Notes

Reaction equation

HRID 1851433 reaction equation
[NH:1]([C:3]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][C:8]=2[NH:14][S:15]([C:18]1[S:19][CH:20]=[CH:21][CH:22]=1)(=[O:17])=[O:16])=[O:4])[NH2:2].[CH:23](OC)(OC)OC>>[O:4]1[CH:23]=[N:2][N:1]=[C:3]1[C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][C:8]=2[NH:14][S:15]([C:18]1[S:19][CH:20]=[CH:21][CH:22]=1)(=[O:17])=[O:16]

Participants

3

Reactant 2

HCID 9005Trimethyl orthoformateHCID 57901816HCID 57901816, compound

Product 1

HCID 136060816HCID 136060816, compoundYield 39%

Conditions

Temperature
100 °C

Procedure

A mixture of N-[2-(hydrazinocarbonyl)-1H-indol-7-yl]thiophene-2-sulfonamide (0.28 g) and trimethyl orthoformate (0.13 g) was stirred at 100° C. overnight. The reaction mixture was concentrated, and the residue was subjected to silica gel column chromatography and the title compound (0.11 g, yield 39%) was obtained as colorless crystals from a fraction eluted with tetrahydrofuran-hexane (1:1, volume ratio). The crystals were recrystallized from ethyl acetate-hexane. melting point 271-272° C. (decomposition).

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-ceb5f298409c445dad463bbc1eeeb38c
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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