Diisopropylamine → HCID 22633006, compound

HRID 2270174Notes

Reaction equation

[Li]CCCC.C(NC(C)C)(C)C.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:19]=[CH:20][CH:21]=1)[NH2:18].F[C:23]1[CH:31]=[C:30]([F:32])[C:29]([F:33])=[CH:28][C:24]=1[C:25]([OH:27])=[O:26]>>[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:19]=[CH:20][CH:21]=1)[NH:18][C:23]1[CH:31]=[C:30]([F:32])[C:29]([F:33])=[CH:28][C:24]=1[C:25]([OH:27])=[O:26]

Participants

Reactant 4

HCID 7912Diisopropylamine

HCID 108243-Methoxyaniline

HCID 5211702,4,5-Trifluorobenzoic acid

HCID 178418339Butyllithium

Product 1

HCID 22633006HCID 22633006, compoundYield 94.4%

Procedure

Using General Method 1, the reaction of 2.5 M solution of n-BuLi in hexanes (21 mL, 53 mmol), diisopropylamine (7.2 mL, 51 mmol), 3-methoxy-aniline (1.91 mL, 17 mmol), and 2,4,5-trifluorobenzoic acid (3.0 g, 17 mmol) provided 4.48 g of the crude title compound.

Sources & evidence

ORD record: ord-f9af60ceaa6a4d579d33c48ffa10b1fb
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06331538B1

Reaction notes

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