Trifluoroacetic acid → 6-[[[1(R)-(4-chlorophenyl)ethyl]amino]carbonyl]-2-(4-fluorophenyl)-3-quinolinepentanoic acid

HRID 927025Notes

Reaction equation

[NH2:1][C:2]1[CH:9]=[CH:8]C(Br)=[CH:6][C:3]=1[CH:4]=O.[F:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=O)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[CH:14][CH:13]=1.C(O[C:35]([C:37](F)(F)F)=[O:36])(C(F)(F)F)=O.CC(O)(C)C.[Cl:46][C:47]1[CH:52]=[CH:51][C:50]([C@H:53]([NH2:55])[CH3:54])=[CH:49][CH:48]=1.C(O)(C(F)(F)F)=O>>[Cl:46][C:47]1[CH:52]=[CH:51][C:50]([C@H:53]([NH:55][C:35]([C:37]2[CH:4]=[C:3]3[C:2](=[CH:9][CH:8]=2)[N:1]=[C:18]([C:15]2[CH:16]=[CH:17][C:12]([F:11])=[CH:13][CH:14]=2)[C:19]([CH2:20][CH2:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[CH:6]3)=[O:36])[CH3:54])=[CH:49][CH:48]=1

Participants

Reactant 5

HCID 6422Trifluoroacetic acid

HCID 1715226(1R)-1-(4-chlorophenyl)ethan-1-amine

HCID 235104752-Amino-5-bromobenzaldehyde

HCID 247268757-(4-Fluorophenyl)-7-oxoheptanoic acid

HCID 86701127TFAA tBuOH

Product 1

HCID 679858526-[[[1(R)-(4-chlorophenyl)ethyl]amino]carbonyl]-2-(4-fluorophenyl)-3-quinolinepentanoic acid

Procedure

In a manner similar to that described previously (Example 1), 2-amino-5-bromobenzaldehyde was sequentially reacted with 7-(4-fluorophenyl)-7-oxoheptanoic acid and TFAA-tBuOH. The resulting ester 5B was converted to 5C (Pd(OAc)2, dcpp-2(HBF)4, K2CO3, 5 atm CO, H2O-DMF, 100° C. overnight), coupled with (R)-1-(4-chlorophenyl)ethanamine (HATU, DIPEA) and deprotected with TFA to provide the title compound, 6-[[[1(R)-(4-chlorophenyl)ethyl]amino]carbonyl]-2-(4-fluorophenyl)-3-quinolinepentanoic acid, 5. LCMS (M+H)=505.

Sources & evidence

ORD record: ord-59ea138ec912463b80940f2b28e1f598
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290453B2

Reaction notes

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