Dichloromethane → HCID 67496302, compound

HRID 1628253Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@H:9]([NH:26]C(=O)OC(C)(C)C)[C:10]([NH:12][C:13]2[S:17][C:16]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([CH3:24])[CH:19]=3)=[N:15][C:14]=2[CH3:25])=[O:11])=[CH:4][CH:3]=1.C(Cl)Cl.C(O)(C(F)(F)F)=O>>[NH2:26][C@@H:9]([CH2:8][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)[C:10]([NH:12][C:13]1[S:17][C:16]([C:18]2[CH:23]=[CH:22][N:21]=[C:20]([CH3:24])[CH:19]=2)=[N:15][C:14]=1[CH3:25])=[O:11]

Participants

Reactant 3

HCID 6344Dichloromethane

HCID 6422Trifluoroacetic acid

HCID 69620786HCID 69620786, compound

Product 1

HCID 67496302HCID 67496302, compoundYield 83.1%

Procedure

To a solution of tert-butyl (S)-3-(4-fluorophenyl)-1-(4-methyl-2-(2-methylpyridin-4-yl)thiazol-5-ylamino)-1-oxopropan-2-ylcarbamate (0.061 g, 0.13 mmol) in DCM (0.0083 ml, 0.13 mmol) was added TFA (0.01 ml, 0.13 mmol). The resulting mixture was allowed to stir at rt overnight. The mixture was concentrated and the residue was purified by HPLC to give 40 mg of (2S)-2-Amino-3-(4-fluorophenyl)-N-(4-methyl-2-(2-methylpyridin-4-yl)thiazol-5-yl)propanamide 22E. 400 MHz 1H NMR (CD3OD) δ: 8.63 (d, J=8.0 Hz, 1H), 8.28 (br s, 1H), 8.22 (dd, J=8.0, 4.0 Hz, 1H), 7.31 (dd, J=8.0, 4.0 Hz, 2H), 7.09 (dd, J=8.0, 8.0 Hz, 2H), 4.51 (dd, J=8.0, 8.0 Hz, 1H), 3.30 (obscured dd, 1H), 3.23 (dd, J=16.0, 8.0 Hz, 1H), 2.80 (s, 3H), 2.43 (s, 3H). LCMS (ES+) m/z 371.

Workup

concentrationThe mixture was concentrated
customthe residue was purified by HPLC

Sources & evidence

ORD record: ord-bfb3b4008dda444ebd319c8d97a8f0a0
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785468B2

Reaction notes

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