Hydrochloric Acid → 1-(2-Amino-5-(thiophen-2-yl)phenyl)-3-isopropylurea

HRID 2201693Notes

Reaction equation

HRID 2201693 reaction equation
Cl.[CH:2]([NH:5][C:6](=[O:27])[NH:7][C:8]1[CH:13]=[C:12]([C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)[CH:11]=[CH:10][C:9]=1[NH:19]C(=O)OC(C)(C)C)([CH3:4])[CH3:3]>O1CCOCC1.CO>[NH2:19][C:9]1[CH:10]=[CH:11][C:12]([C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)=[CH:13][C:8]=1[NH:7][C:6]([NH:5][CH:2]([CH3:4])[CH3:3])=[O:27]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 71007316Tert-butyl (2-(3-isopropylureido)-4-(thiophen-2-yl)phenyl)carbamate

Product 1

HCID 867125261-(2-Amino-5-(thiophen-2-yl)phenyl)-3-isopropylureaYield 91%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A 4M solution of HCl in dioxane (2 mL) was added to a stirred solution of tert-butyl (2-(3-isopropylureido)-4-(thiophen-2-yl)phenyl)carbamate (0.15 g, 0.40 mmol, 1 equiv.) in methanol (4 mL) at 0° C. The reaction was warmed to room temperature and stirred for 2 h. The reaction was then concentrated under reduced pressure. A saturated aqueous solution of sodium bicarbonate was added. The obtained solid was filtered, washed with water and dried to yield 1-(2-amino-5-(thiophen-2-yl)phenyl)-3-isopropylurea (0.10 g, 91% yield). ESI+ MS: m/z 276 ([M+H]+), 1H NMR (500 MHz, d6-DMSO): δ 7.67 (d, J=2.0 Hz, 1H), 7.47 (s, 7.33 (d, J=5.0 Hz, 1H), 7.17 (d, J=3.0 Hz, 1H), 7.09 (dd, J=1.5, 8.0 Hz, 1H), 7.05-7.01 (m, 1H), 6.72 (d, J=8.0 Hz, 1H), 6.08 (d, J=8.0 Hz, 1H), 4.87 (s, 2H), 3.76 (sept, J=7.0 Hz, 1H), 1.10 (d, J=7.0 Hz, 6H).

Workup

  1. concentrationThe reaction was then concentrated under reduced pressure
  2. additionA saturated aqueous solution of sodium bicarbonate was added
  3. filtrationThe obtained solid was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-3a46efb520ee487abaf707952328da94
Source dataset
uspto-grants-2016_06
Patent number
US09365498B2

Reaction notes

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