Hydrochloric Acid → HCID 178465612, compound

HRID 1354397Notes

Reaction equation

HRID 1354397 reaction equation
C(O)(=O)/C=C/C(O)=O.[NH2:9][CH2:10][C@@H:11]([O:18][C:19]1[CH:26]=[C:25]([Cl:27])[C:24]([F:28])=[CH:23][C:20]=1[C:21]#[N:22])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl.[C:30](=[NH:34])(OC)[CH3:31].C(N(CC)CC)C.Cl>C1COCC1.CO.CCOCC.O>[ClH:27].[Cl:27][C:25]1[C:24]([F:28])=[CH:23][C:20]([C:21]#[N:22])=[C:19]([CH:26]=1)[O:18][CH:11]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:10][NH:9][C:30](=[NH:34])[CH3:31]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 10313100Ethanimidic acid, methyl ester, hydrochloride (1:1)HCID 1317264602-[[(1S)-2-Amino-1-phenylethyl]oxy]-4-chloro-5-fluorobenzonitrile (E)-butenedioate

Product 1

HCID 178465612HCID 178465612, compoundYield 99.4%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared by treating the product of Example 1 step (c) (0.2 g) in dry THF (10 ml) with methyl acetimidate hydrochloride (75 mg) followed by triethylamine (0.1 ml) and stirring overnight. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was evaporated and the residue purified by chromatography (silica, 2–20% 7M ammonia in methanol/dichloromethane as eluent) to give a glassy solid. The solid was dissolved in methanol (10 ml), treated with 1M HCl in ether (1 ml) then evaporated. The residue was triturated with ether to give the title compound as a cream solid (90 mg). M.p. 133–135° C.

Workup

  1. customThe title compound was prepared
  2. extractionextracted with ethyl acetate
  3. customThe extract was evaporated
  4. customthe residue purified by chromatography (silica, 2–20% 7M ammonia in methanol/dichloromethane as eluent)
  5. customto give a glassy solid
  6. customthen evaporated
  7. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-74f489f7aaf84e4ca55147812efc8191
Source dataset
uspto-grants-2007_05
Patent number
US07223794B2

Reaction notes

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