Dimethylacetamide → HCID 86718978, compound

HRID 628181Notes

Reaction equation

HRID 628181 reaction equation
C1C2C(CO[C:16]([N:18](C)[N:19]([CH2:21][C:22]3[N:23]([CH2:31][CH2:32][C:33]([OH:35])=[O:34])[C:24]4[C:29]([CH:30]=3)=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH3:20])=O)C3C(=CC=CC=3)C=2C=CC=1.CN(C)C(=O)C>N1CCCCC1>[CH3:20][N:19]([CH2:21][C:22]1[N:23]([CH2:31][CH2:32][C:33]([O-:35])=[O:34])[C:24]2[C:29]([CH:30]=1)=[CH:28][CH:27]=[CH:26][CH:25]=2)[NH:18][CH3:16].[NH2+:23]1[CH2:24][CH2:29][CH2:33][CH2:32][CH2:31]1

Participants

4

Reactant 2

HCID 31374DimethylacetamideHCID 867189802-[[2-[(9H-Fluoren-9-ylmethoxy)carbonyl]-1,2-dimethylhydrazinyl]methyl]-1H-indole-1-propanoic acid2×

Product 1

HCID 86718978HCID 86718978, compound

Reagents, catalysts & solvents 1

HCID 8082PiperidineSolvent

Procedure

Compound 4 was synthesized from Compound 3 as follows. Indole 3 (64.2 mg, 133 μmol) was dissolved in a solution of piperidine in in N,N-dimethylacetamide (20% v/v, 1.31 mL, 2.65 mmol, 20.0 equiv). After 20 min, the solution was purified by C18 silica gel chromatography (0-100% acetonitrile in water). The product was isolated as a colorless oil (28.4 mg, 82.0 μmol, 62%). 1H NMR (400 MHz, 7:5 D2O:CD3CN) δ 7.84 (d, J=7.9 Hz, 1H), 7.76 (d, J=8.3 Hz, 1H), 7.49 (m, 1H), 7.36 (m, 1H), 6.73 (s, 1H), 4.73-4.69 (m, 2H), 4.25 (s, 2H), 3.36-3.29 (m, 4H), 2.86-2.80 (m, 2H), 2.78 (s, 3H), 2.67 (s, 3H), 1.99-1.95 (m, 4H), 1.88-1.83 (m, 2H). 13C NMR (151 MHz, 7:5 D2O:CD3CN) δ 179.80, 137.61, 135.78, 128.40, 122.59, 121.29, 120.50, 110.94, 103.70, 53.86, 45.32, 42.79, 41.43, 38.64, 33.95, 23.07, 22.41, 1.32. HRMS (ESI) calcd for C14H20N3O2 [M-piperidine+H]+: 262.1556. found: 262.1547.

Workup

  1. customthe solution was purified by C18 silica gel chromatography (0-100% acetonitrile in water)

Sources & evidence

ORD record
ord-db8b27dcfc024997a9a7a59cbf5a43be
Source dataset
uspto-grants-2016_04
Patent number
US09310374B2

Reaction notes

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