Diisopropylethylamine → HCID 21091412, compound

HRID 1348582Notes

Reaction equation

HRID 1348582 reaction equation
[NH2:1][C@@H:2]1[C:8](=[O:9])[NH:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[O:4][CH2:3]1.[CH3:14][CH:15]([C:19]([NH:21][CH2:22][C:23]([F:29])([F:28])[C:24]([F:27])([F:26])[F:25])=[O:20])[C:16](O)=[O:17].O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(C(C)C)CC)(C)C>O1CCCC1>[CH3:14][CH:15]([C:19]([NH:21][CH2:22][C:23]([F:28])([F:29])[C:24]([F:25])([F:27])[F:26])=[O:20])[C:16]([NH:1][C@@H:2]1[C:8](=[O:9])[NH:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[O:4][CH2:3]1)=[O:17]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 18599717HCID 18599717, compoundHCID 210724942-Methyl-N-(2,2,3,3,3-pentafluoro-propyl)-malonamic acid

Product 1

HCID 21091412HCID 21091412, compoundYield 39.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.07 g (0.37 mmol) (S)-7-amino-6,7-dihydro-9H-5-oxa-9-aza-benzocyclohepten-8-one in 7 ml tetrahydrofurane were added 0.15 g (0.59 mmol) 2-methyl-N-(2,2,3,3,3-pentafluoro-propyl)-malonamic acid, 0.09 g (0.59 mmol) 1-hydroxybenzotriazole hydrate, 0.12 g (0.59 mmol) N-(3-dimethylaminopropyl)-N′-ethyl-carbodiimid-hydrochloride and 1.0 ml (5.9 mmol) diisopropylethylamine. After stirring at room temperature over night the solvent was removed by distillation and the residue was purified by chromatography on silicagel with ethylacetate/heptane (gradient 0–80/100–20) to yield 0.06 g (23%) 2-methyl-N-((S)-8-oxo-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl)-N′-(2,2,3,3,3-pentafluoro-propyl)-malonamide as light yellow solid, MS m/e (%): 410.3 (M+H+, 100).

Workup

  1. customwas removed by distillation
  2. customthe residue was purified by chromatography on silicagel with ethylacetate/heptane (gradient 0–80/100–20)

Sources & evidence

ORD record
ord-68891e4f15244f72926ace40b9b5d0ad
Source dataset
uspto-grants-2007_05
Patent number
US07211573B2

Reaction notes

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