Triethyl methanetricarboxylate → 1-(3-Trifluoromethyl-benzyl)-4-hydroxy-2-oxo-1,2-dihydro-pyrrolo[1,2-b]pyridazine-3-carboxylic acid ethyl ester

HRID 1511946Notes

Reaction equation

HRID 1511946 reaction equation
C(O[C:6](=[O:24])[N:7]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=1)[N:8]1[CH:12]=[CH:11][CH:10]=[CH:9]1)(C)(C)C.[CH2:25]([O:27][C:28](=[O:40])[CH:29](C(OCC)=O)[C:30](OCC)=[O:31])[CH3:26]>>[CH2:25]([O:27][C:28]([C:29]1[C:6](=[O:24])[N:7]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:21])([F:22])[F:23])[CH:15]=2)[N:8]2[CH:9]=[CH:10][CH:11]=[C:12]2[C:30]=1[OH:31])=[O:40])[CH3:26]

Participants

3

Reactant 2

HCID 80471Triethyl methanetricarboxylateHCID 67230549(3-Trifluoromethyl-benzyl)-pyrrol-1-yl-carbamic acid tert-butyl ester

Product 1

HCID 672306271-(3-Trifluoromethyl-benzyl)-4-hydroxy-2-oxo-1,2-dihydro-pyrrolo[1,2-b]pyridazine-3-carboxylic acid ethyl ester

Procedure

Prepared according to the thermal cyclization condition used in Example 1 step c) from starting materials (3-trifluoromethyl-benzyl)-pyrrol-1-yl-carbamic acid tert-butyl ester (1.0 eq.) and 2-ethoxycarbonyl-malonic acid diethyl ester (3.0 eq.). ESI (m/z): 381 (M+H)+.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-652e36ca2b794d90b53ce68b4f6f98cb
Source dataset
uspto-grants-2012_07
Patent number
US08217043B2

Reaction notes

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