Ethyl 1-aminocyclopropane-1-carboxylate hydrochloride → 4'-(4-chlorophenyl)-3'-methylspiro[cyclopropane-1,6'-isothiazolo[5,4-e][1,4]diazepin]-7'(8'H)-one

HRID 1772349Notes

Reaction equation

HRID 1772349 reaction equation
[NH2:1][C:2]1[S:6][N:5]=[C:4]([CH3:7])[C:3]=1[C:8]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)=O.Cl.[NH2:18][C:19]1([C:22](OCC)=[O:23])[CH2:21][CH2:20]1>N1C=CC=CC=1>[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([C:8]2[C:3]3[C:4]([CH3:7])=[N:5][S:6][C:2]=3[NH:1][C:22](=[O:23])[C:19]3([CH2:21][CH2:20]3)[N:18]=2)=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 386203Ethyl 1-aminocyclopropane-1-carboxylate hydrochlorideHCID 67814140(5-Amino-3-methylisothiazol-4-yl)(4-chlorophenyl)methanone

Product 1

HCID 1363380654'-(4-chlorophenyl)-3'-methylspiro[cyclopropane-1,6'-isothiazolo[5,4-e][1,4]diazepin]-7'(8'H)-oneYield 14.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of (5-amino-3-methylisothiazol-4-yl)(4-chlorophenyl)methanone (0.19 g, 0.75 mmol) and ethyl 1-aminocyclopropanecarboxylate hydrochloride (0.19 g, 1.13 mmol) in pyridine (1 mL) was heated at 170° C. for 18 h. The reaction mixture was then evaporated, extracted with water, dried over Na2SO4, filtered and evaporated. The crude product was purified by flash chromatography (EtOAc/hexane 0:10 to 5:5) to give 4′-(4-chlorophenyl)-3′-methylspiro[cyclopropane-1,6′-isothiazolo[5,4-e][1,4]diazepin]-7′(8′H)-one (35 mg).

Workup

  1. customThe reaction mixture was then evaporated
  2. extractionextracted with water
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was purified by flash chromatography (EtOAc/hexane 0:10 to 5:5)

Sources & evidence

ORD record
ord-589de26fcd2a41738b053402668da37d
Source dataset
uspto-grants-2016_02
Patent number
US09249161B2

Reaction notes

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