Hydrochloric Acid → HCID 57826871, compound

HRID 1845371Notes

Reaction equation

HRID 1845371 reaction equation
CC([N:5]([CH2:9][CH:10]([NH:17][C:18]([C:20]1[S:21][C:22]([C:25]2[N:29]([CH3:30])[N:28]=[CH:27][CH:26]=2)=[CH:23][CH:24]=1)=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)C(=O)[O-])(C)C.Cl.O1CCOCC1>CO>[NH2:5][CH2:9][CH:10]([NH:17][C:18]([C:20]1[S:21][C:22]([C:25]2[N:29]([CH3:30])[N:28]=[CH:27][CH:26]=2)=[CH:23][CH:24]=1)=[O:19])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 86633546HCID 86633546, compound

Product 1

HCID 57826871HCID 57826871, compoundYield 107.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1,1-dimethylethyl[2-({[5-(1-methyl-1H-pyrazol-5-yl)-2-thienyl]carbonyl}amino)-2-phenylethyl]carbamate (56 mg, 0.131 mmol) was dissolved in MeOH (2 mL) and treated with excess 4M HCl in dioxane (656 μL, 2.62 mmol). After 4 h, the solution was concentrated affording the title compound (46 mg, quant.) as a yellow solid: LC-MS (ES) m/z 327 (M+H)+, 1H NMR (d6-DMSO, 400 MHz) δ 9.46 (d, J=8.2 Hz, 1H), 8.27 (bs, 1H), 8.20 (d, J=4.0 Hz, 1H), 7.48-7.75 (m, 3H), 7.37-7.40 (m, 2H), 7.31-7.33 (m, 1H), 6.58 (d, J=1.9 Hz, 1H), 5.21-5.30 (m, 1H), 3.97 (s, 3H), 3.36-3.41 (m, 1H), 3.19-3.25 (m, 1H).

Workup

  1. concentrationthe solution was concentrated

Sources & evidence

ORD record
ord-a815e91f39694d46a3a53f93fe9b00ab
Source dataset
uspto-grants-2015_02
Patent number
US08946278B2

Reaction notes

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