Dichloromethane → HCID 69113924, compound

HRID 749022Notes

Reaction equation

HRID 749022 reaction equation
[CH3:1][O:2][C:3](=[O:33])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH:19]([NH:25]C(OC(C)(C)C)=O)[C:20](=[O:24])[N:21]([CH3:23])[CH3:22])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1.C(Cl)[Cl:35]>>[ClH:35].[CH3:1][O:2][C:3](=[O:33])[CH2:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH:19]([NH2:25])[C:20](=[O:24])[N:21]([CH3:22])[CH3:23])=[CH:14][CH:13]=2)=[CH:10][CH:11]=1

Participants

3

Reactant 2

HCID 6344DichloromethaneHCID 69113915HCID 69113915, compound

Product 1

HCID 69113924HCID 69113924, compoundYield 94.8%

Conditions

Temperature
2.5 °C

Procedure

Amide compound 45 (2.7 g) was dissolved in CH2Cl2 (50 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 2 h. The excess HCl was degassed and the CH2Cl2 was removed. The residual sticky solid was dried under vacuum without further purification to yield the crude hydrochloride salt 53 (2.2 g, 94.8%). 1H NMR (DMSO-d6): 10.55 (b, 1H), 7.61 (d, J=8.0 Hz, 2H), 7.58 (d, J=8.4 Hz, 2H), 7.31 (overlapped d, J=8.4 Hz, 2H), 7.29 (d, J=8.4 Hz, 2H), 4.57 (m, 1H), 3.58 (s, 3H), 2.99-3.20 (m, 2H), 2.88 (t, J=7.6 Hz, 2H), 2.80 (s, 3H), 2.69 (s, 3H), 2.66 (t, J=7.6 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 sticky solid was dried under vacuum without further purification

Sources & evidence

ORD record
ord-1703319c87824bc0acb12fadd0edd52c
Source dataset
uspto-grants-2008_07
Patent number
US07399786B2

Reaction notes

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