Methanol → HCID 57634065, compound

HRID 2109749Notes

Reaction equation

HRID 2109749 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([NH:16][CH2:17][C@@H:18]([NH:30]C(=O)OC(C)(C)C)[CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)[S:5][C:6]=1[C:7]1[S:8][C:9]2[CH:10]=[N:11][CH:12]=[CH:13][C:14]=2[N:15]=1.C(O)(C(F)(F)F)=O.CO>C([SiH](CC)CC)C.C(Cl)Cl>[NH2:30][C@@H:18]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:27])([F:29])[F:28])=[CH:22][CH:21]=1)[CH2:17][NH:16][C:4]1[S:5][C:6]([C:7]2[S:8][C:9]3[CH:10]=[N:11][CH:12]=[CH:13][C:14]=3[N:15]=2)=[C:2]([Br:1])[N:3]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 57634210HCID 57634210, compound

Product 1

HCID 57634065HCID 57634065, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 12052TriethylsilaneCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a 150 mL round-bottomed flask was added tert-butyl (S)-1-(4-bromo-5-(thiazolo[5,4-c]pyridin-2-yl)thiazol-2-ylamino)-3-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate (0.157 g, 0.26 mmol), DCM (25.00 mL, 389 mmol) and TFA (5.00 mL, 65 mmol) with a few drops of triethylsilane, and the resulting solution was stirred for about 15 minutes and followed by LCMS. LCMS showed conversion to product so the solvent was removed, and the oil was dissolved in 2 N ammonia in MeOH and adsorbed on to a plug of silica gel. Chromatography through a Redi-Sep® pre-packed silica gel column (12 g), eluting with a gradient of 1% to 10% 2 M ammonia.MeOH in DCM, provided N-((S)-2-amino-3-(4-(trifluoromethyl)phenyl)propyl)-4-bromo-5-(thiazolo[5,4-c]pyridin-2-yl)thiazol-2-amine (0.086 g, 65% yield).

Workup

  1. customwas removed
  2. dissolutionthe oil was dissolved in 2 N ammonia in MeOH
  3. washChromatography through a Redi-Sep® pre-packed silica gel column (12 g), eluting with a gradient of 1% to 10% 2 M ammonia

Sources & evidence

ORD record
ord-15ca1df60bc44e3faf15ff13cb9ca67b
Source dataset
uspto-grants-2009_04
Patent number
US07514566B2

Reaction notes

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