1-(2,2,2-Trifluoroacetamido)cyclopropane-1-carboxylic acid → HCID 123970855, compound

HRID 2046550Notes

Reaction equation

HRID 2046550 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]([NH2:10])[CH2:8][S:7][C:6]=2[CH:11]=1.[F:12][C:13]([F:24])([F:23])[C:14]([NH:16][C:17]1([C:20](O)=[O:21])[CH2:19][CH2:18]1)=[O:15]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]([NH:10][C:20]([C:17]3([NH:16][C:14](=[O:15])[C:13]([F:12])([F:23])[F:24])[CH2:18][CH2:19]3)=[O:21])[CH2:8][S:7][C:6]=2[CH:11]=1

Participants

3

Reactant 2

HCID 129888001-(2,2,2-Trifluoroacetamido)cyclopropane-1-carboxylic acidHCID 68296717HCID 68296717, compound

Product 1

HCID 123970855HCID 123970855, compound

Procedure

In analogy to the procedure described for the preparation of intermediate A-1 [B] and A-1 [C], (rac)-6-bromo-2,3-dihydro-benzo[b]thiophen-3-ylamine has been coupled with 1-(2,2,2-trifluoroacetamido)cyclopropanecarboxylic acid (intermediate A-1 [A]) to give 1-(2,2,2-trifluoro-acetylamino)-cyclopropanecarboxylic acid ((rac)-6-bromo-2,3-dihydro-benzo[b]thiophen-3-yl)-amide, which was subsequently reacted with 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) to yield the title compound as yellow oil. MS: 455.4 (M−H−).

Sources & evidence

ORD record
ord-2456199191fc4ab7a0056cbd5e7fdc5c
Source dataset
uspto-grants-2013_11
Patent number
US08592426B2

Reaction notes

Loading…