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

HRID 62686Notes

Reaction equation

HRID 62686 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, 1H), 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-4f31079425f643e39b97f7c4868ec797
Source dataset
uspto-grants-2016_09
Patent number
US09447030B2

Reaction notes

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