Trifluoroacetic acid → HCID 67984621, compound

HRID 927026Notes

Reaction equation

HRID 927026 reaction equation
[NH2:1][C:2]1[C:7]([CH:8]=O)=[CH:6]C(Br)=[CH:4][N:3]=1.[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:6]=[C:7]3[C:2](=[N:3][CH:4]=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:8]3)=[O:36])[CH3:54])=[CH:49][CH:48]=1

Participants

6

Reactant 5

HCID 6422Trifluoroacetic acidHCID 1715226(1R)-1-(4-chlorophenyl)ethan-1-amineHCID 242137922-Amino-5-bromo-3-pyridinecarbaldehydeHCID 247268757-(4-Fluorophenyl)-7-oxoheptanoic acidHCID 86701127TFAA tBuOH

Product 1

HCID 67984621HCID 67984621, compound

Procedure

In a manner similar to that described previously (Example 1), 2-amino-5-bromopyridine-3-carboxaldehyde was sequentially reacted with 7-(4-fluorophenyl)-7-oxoheptanoic acid and TFAA-tBuOH. The resulting ester 6B was converted to 6C, coupled with (R)-1-(4-chlorophenyl)ethanamine, and deprotected with TFA to provide the title compound, 6-[[[1(R)-(4-chlorophenyl)ethyl]amino]carbonyl]-2-(4-fluorophenyl)-1,8-naphthyridine-3-pentanoic acid, 6. LCMS (M+H)=506.

Sources & evidence

ORD record
ord-7d468b9cc720462db67eb16e5b11fb20
Source dataset
uspto-grants-2016_03
Patent number
US09290453B2

Reaction notes

Loading…