Cyclopropanemethanamine → HCID 68896630, compound

HRID 1984549Notes

Reaction equation

HRID 1984549 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].[CH:28]1([CH2:31]N)[CH2:30][CH2:29]1.O.O[N:35]1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.Cl.CN(C)CCCN=C=NCC>O1CCCC1>[CH:28]1([CH2:31][N:10]([C@@H:11]2[C:17](=[O:18])[NH:16][C:15]3[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=3[C:13]3[CH:23]=[CH:24][CH:25]=[CH:26][C:12]2=3)[C:9](=[O:27])[C:2]([OH:1])([CH2:6][CH2:7][CH3:8])[C:3]([NH2:35])=[O:4])[CH2:30][CH2:29]1

Participants

7

Reactant 5

HCID 75646CyclopropanemethanamineHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 57713962HCID 57713962, compound

Product 1

HCID 68896630HCID 68896630, compoundYield 62.4%

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 14.9 mg (0.21 mmol) cyclopropanmethylamine in 3 ml tetrahydrofuran were cooled to 0° C. and 28.2 mg (0.21 mmol) 1-hydroxy-benzotriazole hydrate, 71 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 50.0 mg (62%) (R/S)-N-cyclopropylmethyl-2-hydroxy-N-((S)-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)-2-propyl-malonamide: MS (m/e): 422.4 (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-9576f87712a04a7e834705f73bed465e
Source dataset
uspto-grants-2009_06
Patent number
US07544679B2

Reaction notes

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