Hydrochloric Acid → HCID 67446418, compound

HRID 2194915Notes

Reaction equation

HRID 2194915 reaction equation
[C:1]([NH:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[CH:17]=[CH:16][C:15]([CH:18]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][CH2:36][CH2:37][O:38][C:39]3[C:44]([Cl:45])=[CH:43][C:42]([CH3:46])=[CH:41][C:40]=3[Cl:47])=[CH:31][CH:30]=2)[CH2:19][NH:20]C(=O)OC(C)(C)C)=[C:14]([CH3:48])[CH:13]=1)(=[O:3])[CH3:2].Cl>CCOCC.CCOC(C)=O>[ClH:45].[C:1]([NH:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[CH:17]=[CH:16][C:15]([CH:18]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][CH2:36][CH2:37][O:38][C:39]3[C:40]([Cl:47])=[CH:41][C:42]([CH3:46])=[CH:43][C:44]=3[Cl:45])=[CH:31][CH:30]=2)[CH2:19][NH2:20])=[C:14]([CH3:48])[CH:13]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86658861HCID 86658861, compound

Product 1

HCID 67446418HCID 67446418, compound

Reagents, catalysts & solvents 1

HCID 21584169Diethylether ethylacetateSolvent

Procedure

Prepared according to the procedure described in EXAMPLE 2, step 5 using tert-butyl (2-{2′-[(acetylamino)methyl]-3-methylbiphenyl-4-yl}-3-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}propyl)carbamate from step 1 as starting materials. Following flash chromatography the desired material (colorless oil) was dissolved in CH2Cl2/Et2O (1/1). HCl (4M in dioxane) was added in excess and the resulting suspension was triturated with Et2O to afford after filtration the title compounds as an off-white solid. 1H NMR (500 MHz, CD3OD): δ 7.45 (d, 1H), 7.41-7.33 (m, 3H), 7.24 (d, 2H), 7.21 (s, 2H), 7.07 (s, 1H), 6.99 (d, 2H), 6.83 (d, 2H), 4.35-4.29 (m, 6H), 4.23 (d, 1H), 3.68-3.50 (m, 1H), 3.41-3.34 (m, 1H), 3.02 (dd, 1H), 2.87 (dd, 1H), 2.30 (s, 3H), 2.14 (s, 3H), 1.90 (s, 3H).

Workup

  1. customPrepared
  2. customwas triturated with Et2O
  3. customto afford
  4. filtrationafter filtration the title compounds as an off-white solid

Sources & evidence

ORD record
ord-10557725537a4ba89fab1f1649bd5ce5
Source dataset
uspto-grants-2012_12
Patent number
US08334308B2

Reaction notes

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