Dichloromethane → 3-{4-[4-(Aminodimethylcarbamoylmethyl)-phenoxy]-phenyl}-propionamide hydrochloric acid salt

HRID 749010Notes

Reaction equation

HRID 749010 reaction equation
C(OC(=O)[NH:7][CH:8]([C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21]2[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][C:29](=[O:31])[NH2:30])=[CH:23][CH:22]=2)=[CH:16][CH:15]=1)[C:9](=[O:13])[N:10]([CH3:12])[CH3:11])(C)(C)C.C(Cl)[Cl:34]>>[ClH:34].[NH2:7][CH:8]([C:9](=[O:13])[N:10]([CH3:11])[CH3:12])[C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21]2[CH:22]=[CH:23][C:24]([CH2:27][CH2:28][C:29]([NH2:30])=[O:31])=[CH:25][CH:26]=2)=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 6344DichloromethaneHCID 59751109({4-[4-(2-Carbamoylethyl)phenoxy]-phenyl}-dimethylcarbamoylmethyl)-carbamic acid tert-butyl ester

Product 1

HCID 159825833-{4-[4-(Aminodimethylcarbamoylmethyl)-phenoxy]-phenyl}-propionamide hydrochloric acid salt

Conditions

Temperature
2.5 °C

Procedure

The amide compound 38 (0.6 g) was dissolved in CH2Cl2 (30 mL) and cooled to 0-5° C. Hydrogen chloride gas was bubbled through this solution for 20 min. The bubbling was discontinued and the reaction mixture was stirred at room temp for 1 h. The excess HCl was degassed and the CH2Cl2 was removed. The residual solid was triturated with EtOAc (2×50 mL), decanted, and dried to yield the desired compound 39 as a white amorphous solid that was extremely hygroscopic (0.44 g, 86%). 1H NMR (400 MHz, DMSO-d6): 7.47 (d, J=8.8 Hz, 2H), 7.34 (br, 1H), 7.26 (d, J=8.4 Hz, 2H), 7.03 (d, J=8.3 Hz, 2H), 6.95 (d, J=8.4 Hz, 2H), 6.78 (br, 1H), 5.51 (d, J=5.6 Hz, 1H), 2.89 (s, 3H), 2.83 (s, 3H), 2.80 (2.80 (t, J=8.0 Hz,2H), 2.36 (t, J=8.0 Hz, 2H).

Workup

  1. customHydrogen chloride gas was bubbled through this solution for 20 min
  2. customThe excess HCl was degassed
  3. customthe CH2Cl2 was removed
  4. customThe residual solid was triturated with EtOAc (2×50 mL)
  5. customdecanted
  6. customdried

Sources & evidence

ORD record
ord-cb02555a2c264cc49ef9a11c549074e7
Source dataset
uspto-grants-2008_07
Patent number
US07399786B2

Reaction notes

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