Hydrochloric Acid → N-(2-amino-5-(thiophen-2-yl)phenyl)isobutyramide

HRID 2201678Notes

Reaction equation

HRID 2201678 reaction equation
[C:1]([NH:6][C:7]1[CH:12]=[C:11]([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)[CH:10]=[CH:9][C:8]=1[NH:18]C(=O)OC(C)(C)C)(=[O:5])[CH:2]([CH3:4])[CH3:3].Cl.O1CCOCC1>CO>[NH2:18][C:8]1[CH:9]=[CH:10][C:11]([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)=[CH:12][C:7]=1[NH:6][C:1](=[O:5])[CH:2]([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 71007313Tert-butyl (2-isobutyramido-4-(thiophen-2-yl)phenyl)carbamate

Product 1

HCID 86712519N-(2-amino-5-(thiophen-2-yl)phenyl)isobutyramideYield 36%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of tert-butyl (2-isobutyramido-4-(thiophen-2-yl)phenyl)carbamate (0.2 g, 0.52 mmol) in methanol (4 mL) was added 4M HCl in Dioxane (2 mL, 0.53 mmol, 1 equiv.) at 0° C. The reaction was warmed to room temperature and stirred for 2 h. After completion the reaction was concentrated under reduced pressure then basified with a saturated aqueous solution of NaHCO3. The obtained solid was filtered and dried. The crude material was purified by column chromatography (silica gel, MeOH/CH2Cl2) to afford N-(2-amino-5-(thiophen-2-yl)phenyl)isobutyramide (0.05 mg, 36% yield). ESI+ MS: m/z 261 ([M+H]+), 1H NMR (500 MHz, d6-DMSO): δ 9.10 (s, 1H0, 7.5 (s, 1H0, 7.34 (d, J=4.5 Hz, 1H), 7.23-7.19 (m, 2H), 7.05-7.03 (m, 1H0, 6.75 (d, J=8.5 hz, 1H0, 5.03 (s, 2H), 2.67-2.64 (m, 1H), 1.13 (d, J=7 Hz, 6H).

Workup

  1. concentrationAfter completion the reaction was concentrated under reduced pressure
  2. filtrationThe obtained solid was filtered
  3. customdried
  4. customThe crude material was purified by column chromatography (silica gel, MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-3c7f963030f04dcfa4b7039870522207
Source dataset
uspto-grants-2016_06
Patent number
US09365498B2

Reaction notes

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