1-(2,2,2-Trifluoroacetamido)cyclopropane-1-carboxylic acid → 1-(2,2,2-Trifluoro-acetylamino)-cyclopropanecarboxylic acid ((rac)-6-bromo-1,2,3,4-tetrahydro-naphthalen-1-yl)-amide

HRID 2046536Notes

Reaction equation

HRID 2046536 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]([NH2:12])[CH2:7][CH2:6][CH2:5]2.[F:13][C:14]([F:25])([F:24])[C:15]([NH:17][C:18]1([C:21](O)=[O:22])[CH2:20][CH2:19]1)=[O:16]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]([NH:12][C:21]([C:18]1([NH:17][C:15](=[O:16])[C:14]([F:13])([F:24])[F:25])[CH2:19][CH2:20]1)=[O:22])[CH2:7][CH2:6][CH2:5]2

Participants

3

Reactant 2

HCID 129888001-(2,2,2-Trifluoroacetamido)cyclopropane-1-carboxylic acidHCID 707007546-Bromo-1,2,3,4-tetrahydronaphthalen-1-amine

Product 1

HCID 1236543201-(2,2,2-Trifluoro-acetylamino)-cyclopropanecarboxylic acid ((rac)-6-bromo-1,2,3,4-tetrahydro-naphthalen-1-yl)-amide

Procedure

In analogy to the procedure described for the preparation of intermediate A-1 [B] and A-1 [C], (rac)-6-bromo-1,2,3,4-tetrahydronaphthalen-1-amine 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-1,2,3,4-tetrahydro-naphthalen-1-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 light brown oil. MS: 453.2 (MH+).

Sources & evidence

ORD record
ord-ff3e57196a99400a9137060b263a5a19
Source dataset
uspto-grants-2013_11
Patent number
US08592426B2

Reaction notes

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