Trifluoroacetic acid → HCID 51349088, compound

HRID 1968900Notes

Reaction equation

HRID 1968900 reaction equation
C(OC(=O)[NH:7][C@H:8]([CH2:13][N:14]([C:27]1[CH:36]=[CH:35][C:34]2[C:29](=[CH:30][CH:31]=[C:32]([CH:37]3[CH2:39][CH2:38]3)[CH:33]=2)[CH:28]=1)[C:15]([C@@H:17]1[CH2:19][C@H:18]1[C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][N:21]=1)=[O:16])[C@@H:9]([CH3:12])[CH2:10][CH3:11])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][C@@H:8]([C@@H:9]([CH3:12])[CH2:10][CH3:11])[CH2:13][N:14]([C:27]1[CH:36]=[CH:35][C:34]2[C:29](=[CH:30][CH:31]=[C:32]([CH:37]3[CH2:39][CH2:38]3)[CH:33]=2)[CH:28]=1)[C:15]([C@@H:17]1[CH2:19][C@H:18]1[C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][N:21]=1)=[O:16]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67436848HCID 67436848, compound

Product 1

HCID 51349088HCID 51349088, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of [(1S,2S)-1-({(6-cyclopropyl-naphthalen-2-yl)-[trans-2-(5-fluoro-pyridin-2-yl)-cyclopropanecarbonyl]-amino}-methyl)-2-methyl-butyl]-carbamic acid tert-butyl ester in DCM (1.5 mL) was added TFA (0.25 mL) and was stirred at room temperature for 40 mins. The reaction mixture was concentrated, dried under vacuum to afford trans-2-(5-fluoro-pyridin-2-yl)-cyclopropanecarboxylic acid ((2S,3S)-2-amino-3-methyl-pentyl)-(6-cyclopropyl-naphthalen-2-yl)-amide.TFA (14.2 mg, 18% yield in 2 steps) as a tan solid: 1H NMR (400 MHz, MeOD) δ 7.90-7.93 (d, J=12 Hz, 1H), 7.53-7.78 (m, 4H), 7.25-7.32 (m, 2H), 7.10-7.31 (m, 2H), 4.19-4.30 (m, 1H), 3.67-3.75 (m, 1H), 3.20-3.30 (m, 1H), 2.49-2.59 (m, 1H), 1.90-2.01 (m, 1H), 1.75-1.84 (m, 1H), 1.55-1.67 (m, 2H), 1.19-1.31 (m, 2H), 1.07-1.12 (m, 1H), 0.90-0.97 (m, 2H), 0.80-0.90 (m, 3H), 0.25-0.75 (m, 5H); LC/MS (ESI) m/e 446.2 [(M+H)+, calcd for C28H33FN3O 446.6].

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customdried under vacuum

Sources & evidence

ORD record
ord-d71696a54ce444fa9f73513f4d42c759
Source dataset
uspto-grants-2013_04
Patent number
US08426414B2

Reaction notes

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