Dichloromethane → HCID 16004991, compound

HRID 749021Notes

Reaction equation

HRID 749021 reaction equation
C(OC(=O)[NH:7][CH:8]([C:27](=[O:31])[N:28]([CH3:30])[CH3:29])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24](=[O:26])[NH2:25])=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)(C)(C)C.C(Cl)[Cl:34]>>[ClH:34].[NH2:7][CH:8]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:17]=[CH:18][C:19]([CH2:22][CH2:23][C:24](=[O:26])[NH2:25])=[CH:20][CH:21]=2)=[CH:12][CH:11]=1)[C:27]([N:28]([CH3:30])[CH3:29])=[O:31]

Participants

3

Reactant 2

HCID 6344DichloromethaneHCID 69108648HCID 69108648, compound

Product 1

HCID 16004991HCID 16004991, compound

Conditions

Temperature
2.5 °C

Procedure

The amide compound 51 (1.0 g) was dissolved in CH2Cl2 (25 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 temperature 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 52 as a white amorphous solid that was extremely hygroscopic (0.68 g, 79.5%). 1H NMR (DMSO-d6): 7.62 (d, J=8.4 Hz, 2H), 7.57 (d, J=8.0 Hz, 2H), 7.34 (d, J=8.4 Hz, 2H), 7.29 (d, J=8.4 Hz, 2H), 6.78 (br, 1H), 4.58 (m, 1H), 2.95 (m, 2H), 2.81-2.85 (m, 5H), 2.72 (s, 3H), 2.38 (t, J=8.0 Hz, 2H). LCMS (m/e): Obsd. [MH]+ 340, Calcd. 339.4.

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-7e77797ca5a341e2b14be0580055712a
Source dataset
uspto-grants-2008_07
Patent number
US07399786B2

Reaction notes

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