2,2,3,3,3-Pentafluoropropylamine → HCID 87615540, compound

HRID 1984554Notes

Reaction equation

HRID 1984554 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].[F:28][C:29]([F:36])([C:32]([F:35])([F:34])[F:33])[CH2:30]N.O.O[N:39]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]([NH2:39])=[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)[CH2:30][C:29]([F:36])([F:28])[C:32]([F:35])([F:34])[F:33])=[O:27]

Participants

7

Reactant 5

HCID 790022,2,3,3,3-PentafluoropropylamineHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 57713962HCID 57713962, compound

Product 1

HCID 87615540HCID 87615540, compoundYield 63.2%

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 31.2 mg (0.21 mmol) 2,2,3,3,3-pentafluoropropylamine in 3 ml tetrahydrofuran were cooled to 0° C. and 28.2 mg (0.21 mmol) 1-hydroxy-benzotriazole hydrate, 72 μl (0.42 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 60.0 mg (63%) (R/S)-2-hydroxy-N-((S)-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)-N-(2,2,3,3,3-pentafluoro-propyl)-2-propyl-malonamide: MS (m/e): 500.4 (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-10b761a7603744fc8bed92ac15048251
Source dataset
uspto-grants-2009_06
Patent number
US07544679B2

Reaction notes

Loading…