Potassium Carbonate → HCID 67200948, compound

HRID 658284Notes

Reaction equation

HRID 658284 reaction equation
[C:1]([CH:5]([NH:13][NH:14][C:15]([C:17]1[CH:26]=[CH:25][C:20]2[O:21][CH2:22][CH2:23][O:24][C:19]=2[C:18]=1[CH2:27][CH3:28])=[O:16])[CH:6]=[C:7]([CH3:12])[C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:4])([CH3:3])[CH3:2].[CH3:29][O:30][C:31]1[CH:32]=[C:33]([CH:37]=[C:38]([O:41][CH3:42])[C:39]=1[CH3:40])[C:34](Cl)=[O:35].C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[C:1]([CH:5]([N:13]([C:34](=[O:35])[C:33]1[CH:37]=[C:38]([O:41][CH3:42])[C:39]([CH3:40])=[C:31]([O:30][CH3:29])[CH:32]=1)[NH:14][C:15]([C:17]1[CH:26]=[CH:25][C:20]2[O:21][CH2:22][CH2:23][O:24][C:19]=2[C:18]=1[CH2:27][CH3:28])=[O:16])[CH:6]=[C:7]([CH3:12])[C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 226200193,5-Dimethoxy-4-methylbenzoyl chlorideHCID 67068311HCID 67068311, compound

Product 1

HCID 67200948HCID 67200948, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Ethyl-2,3-dihydro-benzo[1,4]dioxine-6-carboxylic acid N′-(1-tert-butyl-3,4,4-trimethyl-pent-2-enyl)-hydrazide (150 mg, 0.39 mmol) and 3,5-dimethoxy-4-methylbenzoyl chloride (83 mg, 0.39 mmol) were dissolved in 5 mL CH2Cl2. 5 mL of 25% K2CO3 were added, and the reaction mixture was stirred at room temperature overnight. The reaction was monitored by TLC. The phases were separated, adding additional CH2Cl2 and/or water as needed to aid manipulation. The CH2Cl2 layer was dried and solvent was removed in vacuo to provide 210 mg of crude product. This material was purified by silica gel column chromatography, eluting with a step gradient of 10-25% ethyl acetate in hexane to yield 3,5-dimethoxy-4-methyl-benzoic acid N-(1-tert-butyl-3,4,4-trimethyl-pent-2-enyl)-N′-(5-ethyl-2,3-dihydro-benzo[1,4]dioxine-6-carbonyl)-hydrazide RG115898 (83 mg, Rf=0.19 in 25% ethyl acetate in n-hexane, yield 38%). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 10.19 (s, 1H), 6.75 (d, J=8.0 Hz, 1H), 6.69 (s, 2H), 6.61 (d, J=8.0 Hz, 1H), 5.43 (d, J=10.0 Hz, 1H), 5.41 (d, 14.4 Hz, 1H), 4.30-4.20 (m, 4H), 3.80 (s, 6H), 2.21-2.15 (m, 1H), 2.01 (s, 3H), 1.81 (m, 1H), 1.76-1.64 (m, 1H), 1.06 (s, 9H), 1.00 (s, 9H), 0.70 (t, J=7.6 Hz, 3H).

Workup

  1. customThe phases were separated
  2. additionadding additional CH2Cl2 and/or water
  3. dry with materialThe CH2Cl2 layer was dried
  4. customsolvent was removed in vacuo
  5. customto provide 210 mg of crude product
  6. customThis material was purified by silica gel column chromatography
  7. washeluting with a step gradient of 10-25% ethyl acetate in hexane

Sources & evidence

ORD record
ord-63cc58ada9a947948ec29eeb35bc7b88
Source dataset
uspto-grants-2011_12
Patent number
US08076454B2

Reaction notes

Loading…