Hydrochloric Acid → HCID 21091512, compound

HRID 1348583Notes

Reaction equation

HRID 1348583 reaction equation
[NH2:1][C@@H:2]1[C:8](=[O:9])[N:7]([CH3:10])[C:6]2[CH:11]=[CH:12][CH:13]=[CH:14][C:5]=2[O:4][CH2:3]1.[F:15][C:16]([F:29])([C:25]([F:28])([F:27])[F:26])[CH2:17][NH:18][C:19](=[O:24])[CH2:20][C:21](O)=[O:22].O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(C(C)C)CC)(C)C.Cl>O1CCCC1>[CH3:10][N:7]1[C:6]2[CH:11]=[CH:12][CH:13]=[CH:14][C:5]=2[O:4][CH2:3][C@H:2]([NH:1][C:21](=[O:22])[CH2:20][C:19]([NH:18][CH2:17][C:16]([F:29])([F:15])[C:25]([F:26])([F:28])[F:27])=[O:24])[C:8]1=[O:9]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 21072520HCID 21072520, compoundHCID 57471845(3S)-3-Amino-2,3-dihydro-5-methyl-1,5-benzoxazepin-4(5H)-one

Product 1

HCID 21091512HCID 21091512, compoundYield 39.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.06 g (0.31 mmol) (S)-7-amino-9-methyl-6,7-dihydro-9H-5-oxa-9-aza-benzocyclohepten-8-one in 5 ml tetrahydrofurane were added 0.07 g (0.31 mmol) N-(2,2,3,3,3-pentafluoro-propyl)-malonamic acid, 0.04 g (0.31 mmol) 1-hydroxybenzotriazole hydrate, 0.06 g (0.31 mmol) N-(3-dimethylaminopropyl)-N′-ethyl-carbodiimid-hydrochloride and 0.1 ml (0.62 mmol) diisopropylethylamine. After stirring at room temperature over night the mixture was added to 1N aqueous hydrochloric acid. Extraction with dichloromethane, followed by washing with saturated aqueous sodium bicarbonate solution and drying with sodium sulfate, and chromatography on silicagel with ethylacetate/heptane yielded 0.05 g (39%) N-((S)-9-methyl-8-oxo-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl)-N′-(2,2,3,3,3-pentafluoro-propyl)-malonamide as white solid, MS m/e (%): 410.3 (M+H+, 100).

Workup

  1. extractionExtraction with dichloromethane
  2. washby washing with saturated aqueous sodium bicarbonate solution
  3. dry with materialdrying with sodium sulfate, and chromatography on silicagel with ethylacetate/heptane

Sources & evidence

ORD record
ord-cd1c55957bbd49508baf3f27d39a6cdb
Source dataset
uspto-grants-2007_05
Patent number
US07211573B2

Reaction notes

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