Hydrochloric Acid → HCID 58464749, compound

HRID 2089460Notes

Reaction equation

HRID 2089460 reaction equation
[F:1][CH:2]([F:33])[CH2:3][N:4]1[CH:8]=[C:7]([NH:9][C:10]([C:12]2[N:13]=[C:14]([C:25]3[C:30]([F:31])=[CH:29][CH:28]=[CH:27][C:26]=3[F:32])[S:15][C:16]=2[NH:17]C(=O)OC(C)(C)C)=[O:11])[CH:6]=[N:5]1.Cl>O1CCOCC1>[NH2:17][C:16]1[S:15][C:14]([C:25]2[C:30]([F:31])=[CH:29][CH:28]=[CH:27][C:26]=2[F:32])=[N:13][C:12]=1[C:10]([NH:9][C:7]1[CH:6]=[N:5][N:4]([CH2:3][CH:2]([F:1])[F:33])[CH:8]=1)=[O:11]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58464891HCID 58464891, compound

Product 1

HCID 58464749HCID 58464749, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

tert-butyl 4-(1-(2,2-difluoroethyl)-1H-pyrazol-4-ylcarbamoyl)-2-(2,6-difluorophenyl)thiazol-5-ylcarbamate was stirred with 4.0M HCl in dioxane overnight. The reaction was concentrated and the residue was basified with sat. sodium bicarbonate. The mixture was extracted with ethyl acetate (3×), concentrated and purified on reverse phase HPLC to afford the title compound 384. 1H NMR (400 MHz, DMSO) δ 9.82 (s, 1H), 8.10 (s, 1H), 7.74 (s, 1H), 7.62-7.39 (m, 3H), 7.26 (dd, J=14.3, 5.9 Hz, 2H), 6.32 (tt, J=54.9, 3.7 Hz, 1H), 4.58 (td, J=15.1, 3.8 Hz, 2H). MS (ESI) m/z: 386.3 [M+H+].

Workup

  1. concentrationThe reaction was concentrated
  2. extractionThe mixture was extracted with ethyl acetate (3×)
  3. concentrationconcentrated
  4. custompurified on reverse phase HPLC

Sources & evidence

ORD record
ord-4b13e5be98154034b998b4fd14f67dc9
Source dataset
uspto-grants-2013_05
Patent number
US08436001B2

Reaction notes

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