Diisopropylethylamine → HCID 86621913, compound

HRID 1984550Notes

Reaction equation

HRID 1984550 reaction equation
[OH:1][C:2]([C:9](=[O:27])[NH:10][C@@H:11]1[C:17](=[O:18])[NH:16][C:15]2[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=2[C:13]2[CH:23]=[CH:24][CH:25]=[CH:26][C:12]1=2)([CH2:6][CH2:7][CH3:8])[C:3](O)=[O:4].Cl.[F:29][C:30]([F:35])([F:34])[CH2:31][CH2:32]N.O.O[N:38]1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.Cl.CN(C)CCCN=C=NCC>O1CCCC1>[OH:1][C:2]([CH2:6][CH2:7][CH3:8])([C:3]([NH2:38])=[O:4])[C:9]([N:10]([C@@H:11]1[C:17](=[O:18])[NH:16][C:15]2[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=2[C:13]2[CH:23]=[CH:24][CH:25]=[CH:26][C:12]1=2)[CH2:32][CH2:31][C:30]([F:35])([F:34])[F:29])=[O:27]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 252105053,3,3-Trifluoropropylamine hydrochlorideHCID 57713962HCID 57713962, compound

Product 1

HCID 86621913HCID 86621913, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 70.0 mg (0.19 mmol) 2-hydroxy-2-((S)-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-ylcarbamoyl)-pentanoic acid and 31.3 mg (0.21 mmol) 3,3,3-trifluoropropylamine hydrochloride in 3 ml tetrahydrofuran were cooled to 0° C. and 28.2 mg (0.21 mmol) 1-hydroxy-benzotriazole hydrate, 103 μl (0.61 mmol) diisopropylethylamine and 40.1 mg (0.21 mmol) N-(3-dimethylaminopropyl)-N′-ethyl-carbodiimide hydrochloride were added. Stirring was continued overnight. Removal of the solvent by distillation and chromatography on silicagel with heptane/ethylacetate (gradient 90:10 to 50:50) yielded 50.0 mg (57%) (R/S)-2-hydroxy-N-((S)-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)-2-propyl-N-(3,3,3-trifluoro-propyl)-malonamide: MS (m/e): 464.0 (M+H)+.

Workup

  1. customRemoval of the solvent
  2. distillationby distillation and chromatography on silicagel with heptane/ethylacetate (gradient 90:10 to 50:50)

Sources & evidence

ORD record
ord-973117450b7344a0878928324e0af397
Source dataset
uspto-grants-2009_06
Patent number
US07544679B2

Reaction notes

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