Hydrochloric Acid → Hydrochloric Acid

HRID 406989Notes

Reaction equation

HRID 406989 reaction equation
[F:1][C:2]([F:42])([F:41])[CH2:3][NH:4][C:5]([NH:7][C:8]1[CH:9]=[C:10]([N:14]2[C:18]3[CH:19]=[CH:20][C:21]([C:23]4[CH:24]=[N:25][N:26]([CH:28]5[CH2:33][CH2:32][N:31](C(OC(C)(C)C)=O)[CH2:30][CH2:29]5)[CH:27]=4)=[CH:22][C:17]=3[N:16]=[CH:15]2)[CH:11]=[CH:12][CH:13]=1)=[O:6].[ClH:43].O1CCOCC1>C(OCC)(=O)C>[NH:31]1[CH2:30][CH2:29][CH:28]([N:26]2[CH:27]=[C:23]([C:21]3[CH:20]=[CH:19][C:18]4[N:14]([C:10]5[CH:9]=[C:8]([NH:7][C:5]([NH:4][CH2:3][C:2]([F:1])([F:42])[F:41])=[O:6])[CH:13]=[CH:12][CH:11]=5)[CH:15]=[N:16][C:17]=4[CH:22]=3)[CH:24]=[N:25]2)[CH2:33][CH2:32]1.[ClH:43]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 67980276tert-butyl 4-(4-{1-[3-({[(2,2,2-trifluoroethyl)amino]carbonyl}amino)phenyl]-1H-benzimidazol-5-yl}-1H-pyrazol-1-yl)piperidine-1-carboxylate

Product 2

HCID 313Hydrochloric AcidHCID 67980152N-{3-[5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-1H-benzimidazol-1-yl]phenyl}-N'-(2,2,2-trifluoroethyl)urea

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 4-(4-{1-[3-({[(2,2,2-trifluoroethyl)amino]carbonyl}amino)phenyl]-1H-benzimidazol-5-yl}-1H-pyrazol-1-yl)piperidine-1-carboxylate (130 mg, 0.22 mmol) in ethyl acetate (2 mL) was added 4.0 M hydrogen chloride in dioxane (0.22 mL, 0.89 mmol). The suspension was stirred at r.t. 2 h. and then concentrated under reduced pressure to afford the desired compound as HCl salt. LCMS (M+H)+: m/z=484.2.

Workup

  1. concentration2 h. and then concentrated under reduced pressure

Sources & evidence

ORD record
ord-7b3117e57a92416290d7226c9397ecc9
Source dataset
uspto-grants-2014_06
Patent number
US08754114B2

Reaction notes

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