1-(2,2,2-Trifluoroacetamido)cyclopropane-1-carboxylic acid → 1-(2,2,2-trifluoro-acetylamino)-cyclopropanecarboxylic acid ((S)-5-bromo-indan-1-yl)-amide

HRID 2046533Notes

Reaction equation

HRID 2046533 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C@@H:7]([NH2:11])[CH2:6][CH2:5]2.[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]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C@@H:7]([NH:11][C:20]([C:17]1([NH:16][C:14](=[O:15])[C:13]([F:12])([F:23])[F:24])[CH2:18][CH2:19]1)=[O:21])[CH2:6][CH2:5]2

Participants

3

Reactant 2

HCID 129888001-(2,2,2-Trifluoroacetamido)cyclopropane-1-carboxylic acidHCID 28206724(S)-5-bromo-2,3-dihydro-1H-inden-1-amine

Product 1

HCID 866757721-(2,2,2-trifluoro-acetylamino)-cyclopropanecarboxylic acid ((S)-5-bromo-indan-1-yl)-amide

Procedure

In analogy to the procedure described for the preparation of intermediate A-1 [B] and A-1 [C], (S)-5-bromo-indan-1-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 ((S)-5-bromo-indan-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 solid. MS: 439.3 (MH+).

Sources & evidence

ORD record
ord-a122ae10abbc47eab0dbca797edda8d4
Source dataset
uspto-grants-2013_11
Patent number
US08592426B2

Reaction notes

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