HCID 17823976, compound → HCID 22990217, compound

HRID 1169387Notes

Reaction equation

HRID 1169387 reaction equation
[ClH:1].C(O[C:5]([C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([C:16]2[CH2:17][CH2:18][O:19][C:20]3[CH:26]=[CH:25][C:24]([C:27]4[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=4)=[CH:23][C:21]=3[CH:22]=2)=[O:15])=[CH:9][CH:8]=1)=[NH:6])C.[NH3:34].C(O)C>>[ClH:1].[C:5]([C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([C:16]2[CH2:17][CH2:18][O:19][C:20]3[CH:26]=[CH:25][C:24]([C:27]4[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=4)=[CH:23][C:21]=3[CH:22]=2)=[O:15])=[CH:9][CH:8]=1)(=[NH:34])[NH2:6]

Participants

3

Reactant 2

HCID 17823976HCID 17823976, compoundHCID 22020343Ethanol, reaction products with ammonia, distn. residues

Product 1

HCID 22990217HCID 22990217, compound

Procedure

To N-[4-(ethoxycarbonimidoyl)phenyl]-7-(4-methylphenyl)-2,3-dihydro-1-benzooxepine-4-carboxamide hydrochloride (364 mg) was added a solution of 14% ammonia/ethanol (5 ml). The resulting mixture was stirred at room temperature overnight and then at 50° C. for 3 hours. The reaction mixture was concentrated, the residue was suspended in ethyl acetate and 4 N hydrochloric acid/ethyl acetate was added. The precipitate was collected by filtration, was washed with ethyl acetate and further was recrystallized from acetonitrile/methanol/ethyl acetate to obtain N-(4-amidinophenyl)-7-(4-methylphenyl)-2,3-dihydro-1-benzooxepine-4-carboxamide hydrochloride (compound 42) (127 mg) as colorless crystals.

Workup

  1. waitat 50° C. for 3 hours
  2. concentrationThe reaction mixture was concentrated
  3. addition4 N hydrochloric acid/ethyl acetate was added
  4. filtrationThe precipitate was collected by filtration
  5. washwas washed with ethyl acetate
  6. customfurther was recrystallized from acetonitrile/methanol/ethyl acetate

Sources & evidence

ORD record
ord-b2267e521034419f8153187dc347ac7d
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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