Tetrahydrofuran → Acetic Anhydride

HRID 479671Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[N:16]([C:20](=[O:22])[CH3:21])[N:15]=[CH:14]3)[S:9][CH:10]=1)=[O:5])[CH3:2].CCN(CC)CC.C1C[O:33]CC1>>[C:20]([N:16]1[C:17]2[C:13](=[CH:12][C:11]([C:8]3[S:9][CH:10]=[C:6]([C:4]([OH:5])=[O:3])[N:7]=3)=[CH:19][CH:18]=2)[CH:14]=[N:15]1)(=[O:22])[CH3:21].[CH3:6][C:4]([O:3][C:1]([CH3:2])=[O:33])=[O:5]

Participants

Reactant 3

HCID 8028Tetrahydrofuran

HCID 8471Triethylamine

HCID 69411765HCID 69411765, compound

Product 2

HCID 7918Acetic Anhydride

HCID 18772050HCID 18772050, compound

Procedure

In a manner similar to Preparation CW from 2-(1-acetyl-1H-indazol-5-yl)-thiazole-4-carboxylic acid ethyl ester to give 2-(1-acetyl-1H-indazol-5-yl)-thiazole-4-carboxylic acid as a yellow solid following re-protection with Ac2O, Et3N, and THF. MS m/z: 286.1 (M−H). Calc'd for C13H9N3O3S 287.29.

Sources & evidence

ORD record: ord-191639208c31497ca5dcfc8caf7f25aa
Source dataset: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06645990B2

Reaction notes

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