Hydrochloric Acid → HCID 58464763, compound

HRID 1185405Notes

Reaction equation

HRID 1185405 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]2[N:12]([CH3:13])[N:11]=[CH:10][C:9]=2[NH:14][C:15]([C:17]2[N:18]=[C:19]([C:30]3[C:35]([F:36])=[CH:34][CH:33]=[CH:32][C:31]=3[F:37])[S:20][C:21]=2[NH:22]C(=O)OC(C)(C)C)=[O:16])[CH2:4][CH2:3]1.Cl>O1CCOCC1>[NH2:22][C:21]1[S:20][C:19]([C:30]2[C:35]([F:36])=[CH:34][CH:33]=[CH:32][C:31]=2[F:37])=[N:18][C:17]=1[C:15]([NH:14][C:9]1[CH:10]=[N:11][N:12]([CH3:13])[C:8]=1[CH:5]1[CH2:6][CH2:7][CH:2]([NH2:1])[CH2:3][CH2:4]1)=[O:16]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67437763HCID 67437763, compound

Product 1

HCID 58464763HCID 58464763, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl 4-(5-(4-aminocyclohexyl)-1-methyl-1H-pyrazol-4-ylcarbamoyl)-2-(2,6-difluorophenyl)thiazol-5-ylcarbamate was stirred with 4.0M HCl in dioxane (5 mL) for 2 h. Solvent was removed in vacuo, and the residue was basified with sat. sodium bicarbonate and extracted with ethyl acetate 3×. Combined organic layers were concentrated and purified via reverse phase HPLC to give 369. 1H NMR (400 MHz, DMSO) δ 8.82 (s, 1H), 8.35 (s, 1H), 7.60-7.36 (m, 3H), 7.27 (t, J=8.7 Hz, 1H), 3.80 (s, 3H), 2.77 (t, J=12.3 Hz, 1H), 2.13-1.94 (m, 2H), 1.67 (dt, J=29.6, 13.3 Hz, 5H). MS (ESI) m/z: 433.2 [M+H+].

Workup

  1. customSolvent was removed in vacuo
  2. extractionextracted with ethyl acetate 3×
  3. concentrationCombined organic layers were concentrated
  4. custompurified via reverse phase HPLC

Sources & evidence

ORD record
ord-54a6805e38484baeae7db1191bbe56bc
Source dataset
uspto-grants-2014_03
Patent number
US08669361B2

Reaction notes

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