Trifluoroacetic acid → (2s,4r)-4-(3-Fluoro-4-(5-(1-phenylcyclopropyl)-thiazolo[5,4-b]pyridine-2-yl)phenyl)pyrrolidine-2-carboxylic acid trifluoroacetic acid salt

HRID 1177536Notes

Reaction equation

HRID 1177536 reaction equation
C(OC([N:8]1[CH2:12][C@@H:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[S:20][C:21]4[C:26]([N:27]=3)=[CH:25][CH:24]=[C:23]([C:28]3([C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)[CH2:30][CH2:29]3)[N:22]=4)=[C:15]([F:37])[CH:14]=2)[CH2:10][C@H:9]1[C:38]([OH:40])=[O:39])=O)(C)(C)C.[F:41][C:42]([F:47])([F:46])[C:43]([OH:45])=[O:44]>C(Cl)Cl>[F:41][C:42]([F:47])([F:46])[C:43]([OH:45])=[O:44].[F:37][C:15]1[CH:14]=[C:13]([C@@H:11]2[CH2:12][NH:8][C@H:9]([C:38]([OH:40])=[O:39])[CH2:10]2)[CH:18]=[CH:17][C:16]=1[C:19]1[S:20][C:21]2[C:26]([N:27]=1)=[CH:25][CH:24]=[C:23]([C:28]1([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:29][CH2:30]1)[N:22]=2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67112876(2S,4R)-1-(tert-butoxycarbonyl)-4-(3-fluoro-4-(5-(1-phenyl-cyclopropyl)-thiazolo[5,4-b]pyridine-2-yl)phenyl)pyrrolidine-2-carboxylic acid

Product 1

HCID 67111535(2s,4r)-4-(3-Fluoro-4-(5-(1-phenylcyclopropyl)-thiazolo[5,4-b]pyridine-2-yl)phenyl)pyrrolidine-2-carboxylic acid trifluoroacetic acid salt

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a slurry of (2S,4R)-1-(tert-butoxycarbonyl)-4-(3-fluoro-4-(5-(1-phenyl-cyclopropyl)-thiazolo[5,4-b]pyridine-2-yl)phenyl)pyrrolidine-2-carboxylic acid (0.091 g, 0.16 mmol) in 2 mL DCM was added trifluoroacetic acid (0.13 mL, 1.6 mmol) to give a yellow solution. Upon completion the reaction mixture was concentrated in vacuo and the material was triturated with MTBE to give (2S,4R)-4-(3-fluoro-4-(5-(1-phenylcyclopropyl)-thiazolo[5,4-b]pyridine-2-yl)phenyl)pyrrolidine-2-carboxylic acid trifluoroacetic acid salt. MS (ESI) m/z: Calculated: 459.1; Observed: 459.8 (M++1). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.22-8.36 (m, 2 H), 7.57 (d, J=13.1 Hz, 1 H), 7.27-7.49 (m, 8 H), 7.05 (d, J=8.6 Hz, 1 H), 4.42 (dd, J=10.0, 7.6 Hz, 1 H), 3.59-3.81 (m, 2 H), 3.24-3.34 (m, 1 H), 2.72-2.85 (m, 1 H), 2.06-2.22 (m, 1 H), 1.62-1.74 (m, 2 H), 1.34-1.45 (m, 2 H)

Workup

  1. customto give a yellow solution
  2. concentrationUpon completion the reaction mixture was concentrated in vacuo
  3. customthe material was triturated with MTBE

Sources & evidence

ORD record
ord-b4221f80f09c43a29b400d532cc22c85
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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