Dichloromethane → HCID 67496839, compound

HRID 1628206Notes

Reaction equation

HRID 1628206 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@H:9]([NH:24]C(=O)OC(C)(C)C)[C:10](=[O:23])[NH:11][C:12]2[S:16][C:15]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)=[N:14][CH:13]=2)=[CH:4][CH:3]=1.C(Cl)Cl.C(O)(C(F)(F)F)=O>>[NH2:24][C@@H:9]([CH2:8][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)[C:10]([NH:11][C:12]1[S:16][C:15]([C:17]2[CH:18]=[CH:19][N:20]=[CH:21][CH:22]=2)=[N:14][CH:13]=1)=[O:23]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 67497612HCID 67497612, compound

Product 1

HCID 67496839HCID 67496839, compoundYield 75%

Procedure

To a solution of (S)-tert-butyl 3-(4-fluorophenyl)-1-oxo-1-(2-(pyridin-4-yl)thiazol-5-ylamino)propan-2-ylcarbamate (0.250 g, 0.565 mmol) in DCM (10.0 ml, 155 mmol) was added TFA (2.50 ml, 32.4 mmol). The resulting mixture was allowed to stir at rt for 4 hours. The mixture was concentrated and the residue was purified by HPLC to give 145 mg of (S)-2-amino-3-(4-fluorophenyl)-N-(2-(pyridin-4-yl)thiazol-5-yl)propanamide 5.2B. 400 MHz 1H NMR (CD3OD) δ: 8.79 (d, J=8.0 Hz, 2H), 8.37 (d, J=8.0 Hz, 2H), 7.86 (s, 1H), 7.30 (dd, J=8.0, 4.0 Hz, 2H), 7.08 (dd, J=12, 8.0 Hz, 2H), 4.37 (dd, J=8.0, 8.0 Hz, 1H), 3.34 (obscured dd, 1H), 3.23 (dd, J=12.0, 8.0 Hz, 1H), LCMS (ES+) m/z 343.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-4dd06c7364034e708a3df60c21b29edb
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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