Hydrochloric Acid → HCID 22052282, compound

HRID 1827329Notes

Reaction equation

HRID 1827329 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][N:8]([C:29](=[O:41])[CH2:30][C:31]2[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:33][CH:32]=2)[CH:9]([C:11]2[N:20]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[C:19](=[O:28])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]=2)[CH3:10])[CH:2]=1.[ClH:42].CCOCC>ClCCl>[ClH:42].[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][N:8]([C:29](=[O:41])[CH2:30][C:31]2[CH:32]=[CH:33][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:35][CH:36]=2)[CH:9]([C:11]2[N:20]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[C:19](=[O:28])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]=2)[CH3:10])[CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 22052244HCID 22052244, compound

Product 1

HCID 22052282HCID 22052282, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 3.02 (50 mg, 89 μmol, 1.0 equiv) in 2 mL of dichloromethane was added a 1.0 M solution of HCl in ether (180 μL, 0.18 mmol, 2.0 equiv) dropwise via syringe, followed by another 5 mL of ether. The resulting suspension was stirred at room temperature for 1 h. The precipitates were collected by filtration. The solids were washed twice with 30 mL of ether and air dried in the dark to give 47 mg of the product as a white powder. mp 122.7° C. At room temperature, this compound exists as a mixture of cis/trans amide rotamers, ca. 0.93:1 by 1H NMR (DMSO-d6, T=25° C.) δ 5.05 (q, J=6.8 Hz, 1H) & 5.18 (q, J=6.8 Hz, 1H) ppm. MS (ESI+) m/z 561.2 [M+H]+.

Workup

  1. filtrationThe precipitates were collected by filtration
  2. washThe solids were washed twice with 30 mL of ether and air
  3. customdried in the dark

Sources & evidence

ORD record
ord-8a46d2822c374f20b73eeda554ba966e
Source dataset
uspto-grants-2006_05
Patent number
US07053215B2

Reaction notes

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