Trifluoroacetic acid → 3-(2-Amino-5-(thiophen-2-yl)phenyl)-1,1-dimethylurea

HRID 2201705Notes

Reaction equation

HRID 2201705 reaction equation
[CH3:1][N:2]([CH3:25])[C:3](=[O:24])[NH:4][C:5]1[CH:10]=[C:9]([C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)[CH:8]=[CH:7][C:6]=1[NH:16]C(=O)OC(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[NH2:16][C:6]1[CH:7]=[CH:8][C:9]([C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)=[CH:10][C:5]=1[NH:4][C:3](=[O:24])[N:2]([CH3:1])[CH3:25]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71007375Tert-butyl (2-(3,3-dimethylureido)-4-(thiophen-2-yl)phenyl)carbamate

Product 1

HCID 867125363-(2-Amino-5-(thiophen-2-yl)phenyl)-1,1-dimethylureaYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (2-(3,3-dimethylureido)-4-(thiophen-2-yl)phenyl)carbamate (115 mg, 0.32 mmol) in dichloromethane (5 mL) was added TFA (2 mL) at 0° C. The reaction was warmed to room temperature and stirred for 1h. The reaction was concentrated. The crude residue was diluted with ethyl acetate (30 mL) and washed with a saturated aqueous solution of sodium bicarbonate, then water (20 mL), dried over sodium sulfate, filtered and concentrated. The obtained residue was washed with hexane (2 mL) to afford 3-(2-amino-5-(thiophen-2-yl)phenyl)-1,1-dimethylurea (65 mg, 83% yield). ESI+ MS: m/z 262 ([M]+). 1H NMR (500 MHz, d6-DMSO): δ 7.68 (s, 1H), 7.34 (d, J=5.0, 1H), 7.29 (d, J=2.0, 1H), 7.19 (dd, J=4.5, 2.0, 2H), 7.04 (m, 1H), 6.73 (d, J=8.5, 1H), 5.00 (s, 2H), 2.93 (s, 6H).

Workup

  1. concentrationThe reaction was concentrated
  2. additionThe crude residue was diluted with ethyl acetate (30 mL)
  3. washwashed with a saturated aqueous solution of sodium bicarbonate
  4. dry with materialwater (20 mL), dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. washThe obtained residue was washed with hexane (2 mL)

Sources & evidence

ORD record
ord-f1302c8c23794034ac98bd1e4203f508
Source dataset
uspto-grants-2016_06
Patent number
US09365498B2

Reaction notes

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