Hydrochloric Acid → HCID 58465050, compound

HRID 2089376Notes

Reaction equation

HRID 2089376 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[S:10][C:11]([NH:36]C(=O)OC(C)(C)C)=[C:12]([C:14](=[O:35])[NH:15][C:16]2[CH:17]=[N:18][N:19]([CH3:34])[C:20]=2[C:21]2[CH2:22][CH2:23][N:24](C(OC(C)(C)C)=O)[CH2:25][CH:26]=2)[N:13]=1.Cl>CO.O1CCOCC1>[NH2:36][C:11]1[S:10][C:9]([C:3]2[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=2[F:8])=[N:13][C:12]=1[C:14]([NH:15][C:16]1[CH:17]=[N:18][N:19]([CH3:34])[C:20]=1[C:21]1[CH2:22][CH2:23][NH:24][CH2:25][CH:26]=1)=[O:35]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67438282HCID 67438282, compound

Product 1

HCID 58465050HCID 58465050, compoundYield 96.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

Tert-butyl 2-(2,6-difluorophenyl)-4-(1-methyl-5-(tert-butyloxycarbonyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrazol-4-ylcarbamoyl)thiazol-5-ylcarbamate (0.10 g, 0.16 mmol) was dissolved in MeOH (3 mL) and HCl in 1,4-dioxane (4.0 M, 3 mL) was added. The mixture was stirred at room temperature for 18 hr. The solvents were removed under reduced pressure and the crude residue was re-dissolved in MeOH and loaded onto an SCX column. The column was washed with MeOH and eluted with 7 N ammonia in MeOH to give 258 as a yellow solid (64 mg, 95%). 1H NMR (400 MHz, CDCl3) δ 8.69 (s, 1H), 8.06 (s, 1H), 7.36-7.29 (m, 1H), 7.02 (t, J=8.9 Hz, 2H), 6.12 (s, 2H), 6.01 (s, 1H), 3.82 (s, 3H), 3.61 (d, J=3.4 Hz, 2H), 3.14 (t, J=5.5 Hz, 2H), 2.34 (s, 3H). LCMS (ES+) m/z 417 (M+1)

Workup

  1. customThe solvents were removed under reduced pressure
  2. dissolutionthe crude residue was re-dissolved in MeOH
  3. washThe column was washed with MeOH
  4. washeluted with 7 N ammonia in MeOH

Sources & evidence

ORD record
ord-22c727707651429cae108ec8eeafa9c4
Source dataset
uspto-grants-2013_05
Patent number
US08436001B2

Reaction notes

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