Hydrochloric Acid → HCID 11960891, compound

HRID 1172894Notes

Reaction equation

HRID 1172894 reaction equation
[CH2:1]([NH:8][C:9](=[O:42])[CH2:10][C:11]1[CH:41]=[CH:40][C:14]2[CH:15]=[C:16]([C:18]([NH:20][C:21]3[C:25]([NH:26]C(=O)OC(C)(C)C)=[CH:24][N:23]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[N:22]=3)=[O:19])[S:17][C:13]=2[CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C(OCC)(=O)C.CO.O1CCOCC1>[NH2:26][C:25]1[C:21]([NH:20][C:18]([C:16]2[S:17][C:13]3[CH:12]=[C:11]([CH2:10][C:9]([NH:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[O:42])[CH:41]=[CH:40][C:14]=3[CH:15]=2)=[O:19])=[N:22][N:23]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:24]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 86626027HCID 86626027, compound

Product 1

HCID 11960891HCID 11960891, compoundYield 40%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of crude tert-butyl {3-[({6-[2-(benzylamino)-2-oxoethyl]-1-benzothien-2-yl}carbonyl)amino]-1-phenyl-1H-pyrazol-4-yl}carbamate (from step A) in ethyl aceate (10 mL) and methanol (10 mL) was added 4M HCl in dioxane (10 mL) and the resulting solution was stirred for 16 hours at ambient temperature. The reaction was evaporated to dryness and purified by reverse phase LC to give 148 mg (40%, 2 steps) of N-(4-amino-1-phenyl-1H-pyrazol-3-yl)-6-[2-(benzylamino)-2-oxoethyl]-1-benzothiophene-2-carboxamide as a white solid. 1H NMR (DMSO-d6) δ 11.01 (s, 1H), 8.59 (t, J=5.87 Hz, 1H), 8.35 (s, 1H), 7.89 (t, J=3.82 Hz, 2H), 7.80 (s, 1H), 7.67 (d, J=7.92 Hz, 2H), 7.42 (t, J=7.33 Hz, 2H), 7.36 (d, J=9.1 Hz, 1H), 7.28 (t, J=7.92 Hz, 2H), 7.19 (m, 4H), 4.25 (d, J=5.87 Hz, 2H), 3.61 (s, 2H). ESIMS calcd 482.2 (M++H), found 482.1 (M++H).

Workup

  1. customThe reaction was evaporated to dryness
  2. custompurified by reverse phase LC

Sources & evidence

ORD record
ord-a549bce581914286847ea983d0e76ed8
Source dataset
uspto-grants-2010_11
Patent number
US07834034B2

Reaction notes

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