Water → HCID 86683004, compound

HRID 1497169Notes

Reaction equation

HRID 1497169 reaction equation
C1C2C(COC([NH:18][NH:19][C:20]([C:22]3[C:23](Cl)=[N:24][C:25]4[C:30]([C:31]=3[C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:29][C:28]([Cl:38])=[CH:27][CH:26]=4)=[O:21])=O)C3C(=CC=CC=3)C=2C=CC=1.[NH:40]1[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]1.C(N(CC)CC)C.O>CN(C=O)C>[Cl:38][C:28]1[CH:29]=[C:30]2[C:25](=[CH:26][CH:27]=1)[N:24]=[C:23]([N:40]1[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]1)[C:22]([C:20]([NH:19][NH2:18])=[O:21])=[C:31]2[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8082PiperidineHCID 8471TriethylamineHCID 86683003HCID 86683003, compound

Product 1

HCID 86683004HCID 86683004, compoundYield 38.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of N′-(2,6-dichloro-4-phenyl-quinoline-3-carbonyl)-hydrazinecarboxylic acid 9H-fluoren-9-ylmethyl ester (130 mg, 211 μmol, Eq: 1.00), piperidine (180 mg, 209 μl, 2.11 mmol, Eq: 10) and triethylamine (64.1 mg, 88.2 μl, 633 μmol, Eq: 3) in DMF (2 ml) was heated to 120° C. for 20 min in a microwave. Water was added and the mixture was extracted with ethyl acetate (3×). The combined extracts were washed with water and brine, dried with Na2SO4 and evaporated. The remaining residue was purified by column chromatography (silica gel, DCM/EtOAc 9:1-4:1) to afford the title compound as light yellow solid (31 mg). MS (ESI): 381.2 (M+H)+.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×)
  2. washThe combined extracts were washed with water and brine
  3. dry with materialdried with Na2SO4
  4. customevaporated
  5. customThe remaining residue was purified by column chromatography (silica gel, DCM/EtOAc 9:1-4:1)

Sources & evidence

ORD record
ord-8a1132c731ef43ab8a53eafa69229522
Source dataset
uspto-grants-2015_12
Patent number
US09199938B2

Reaction notes

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