Hydrochloric Acid → HCID 90370305, compound

HRID 2176048Notes

Reaction equation

HRID 2176048 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:35]=[CH:36][CH:37]=2)[C:11]([NH:13][C:14]2[S:15][C:16]3[CH2:34][CH2:33][CH2:32][CH2:31][C:17]=3[C:18]=2[C:19]([NH:21][C:22]2[CH:30]=[CH:29][C:25]([C:26]([OH:28])=O)=[CH:24][CH:23]=2)=[O:20])=[O:12])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH2:38]([N:40]([CH2:48][CH3:49])[C:41]1[CH:46]=[CH:45][C:44]([NH2:47])=[CH:43][CH:42]=1)[CH3:39].CCN=C=NCCCN(C)C.[ClH:61].C1C=CC2N(O)N=NC=2C=1.Cl.C(OCC)(=O)C>CO.O.C(Cl)Cl>[ClH:61].[ClH:61].[CH2:48]([N:40]([CH2:38][CH3:39])[C:41]1[CH:46]=[CH:45][C:44]([NH:47][C:26]([C:25]2[CH:29]=[CH:30][C:22]([NH:21][C:19]([C:18]3[C:17]4[CH2:31][CH2:32][CH2:33][CH2:34][C:16]=4[S:15][C:14]=3[NH:13][C:11](=[O:12])[C:10]3[CH:35]=[CH:36][CH:37]=[C:8]([CH2:7][N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)[CH:9]=3)=[O:20])=[CH:23][CH:24]=2)=[O:28])=[CH:43][CH:42]=1)[CH3:49]

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 7120N,N-Diethyl-p-phenylenediamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 21866389Hydrogen chloride-ethyl acetateHCID 90370210HCID 90370210, compound

Product 1

HCID 90370305HCID 90370305, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 150 mg of 4-{[(2-{[3-(morpholin-4-ylmethyl)benzoyl]amino}-4,5,6,7-tetrahydro-1-benzothiophen-3-yl)carbonyl]amino}benzoic acid, 57 mg of N,N-diethyl-p-phenylenediamine, 61 mg of WSC.hydrochloride, 42 mg of HOBt, and 1.5 mL of methylene chloride was stirred for 3 hours at room temperature. Water was added to the reaction mixture, followed by extraction with methylene chloride. The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified by basic silica gel column chromatography (2% methanol/chloroform), thereby obtaining an oily material. Methanol and 4.0 M hydrogen chloride/ethyl acetate solution were added to this material, and the solution was concentrated under reduced pressure. The residue was treated with ethyl acetate, thereby obtaining 85 mg of N-(4-{[4-(diethylamino)phenyl]carbamoyl}phenyl)-2-{[3-(morpholin-4-ylmethyl)benzoyl]amino}-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide dihydrochloride.

Workup

  1. extractionfollowed by extraction with methylene chloride
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was purified by basic silica gel column chromatography (2% methanol/chloroform)
  5. customobtaining an oily material
  6. concentrationthe solution was concentrated under reduced pressure
  7. additionThe residue was treated with ethyl acetate

Sources & evidence

ORD record
ord-436f89e9ac8d4116af69d529234e184d
Source dataset
uspto-grants-2015_06
Patent number
US09062032B2

Reaction notes

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