Oxygen → HCID 178481257, compound

HRID 2240640Notes

Reaction equation

HRID 2240640 reaction equation
C(OC(=O)[NH:6][C:7]1([C:10]2[CH:15]=[CH:14][C:13]([C:16]([NH:27][C:28]3[CH:33]=[CH:32][C:31]([C:34]4[N:35]=[CH:36][N:37]([CH3:39])[CH:38]=4)=[CH:30][CH:29]=3)=[C:17]3[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=4[O:19][C:18]3=[O:26])=[CH:12][CH:11]=2)[CH2:9][CH2:8]1)C=C.O=O.C(NCC)C>ClCCl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:6][C:7]1([C:10]2[CH:15]=[CH:14][C:13]([C:16]([NH:27][C:28]3[CH:33]=[CH:32][C:31]([C:34]4[N:35]=[CH:36][N:37]([CH3:39])[CH:38]=4)=[CH:30][CH:29]=3)=[C:17]3[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=4[O:19][C:18]3=[O:26])=[CH:12][CH:11]=2)[CH2:8][CH2:9]1

Participants

6

Reactant 3

HCID 977OxygenHCID 8021DiethylamineHCID 178459817HCID 178459817, compound

Product 1

HCID 178481257HCID 178481257, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

0.58 g of allyl(1-{4-[[4-(1-methyl-1H-imidazol-4-yl)phenylamino]-(2-oxobenzofuran-3-ylidene)methyl]phenyl}cyclopropyl)carbamate was dissolved in 20 mL of dichloromethane. The solution was freed from oxygen using argon. Then at RT, 0.52 mL of diethylamine and 0.058 g of tetrakis(triphenylphosphine)palladium (0) were added. The mixture was stirred for 2 hours at RT, the suspension was evaporated down with silica gel and chromatographed with dichloromethane/methanol (97:3) on silica gel 70 at a flow rate of 30 mL/min. The clean fractions were combined, evaporated down to the residue, dissolved in dichloromethane, filtered, and combined with diisopropyl ether. The dichloromethane was distilled off, the crystals formed were suction filtered and washed with diisopropyl ether. Yield: 0.26 g of yellow crystals, melting point 190° C.-191° C., as base. Rf value: 0.51 (dichloromethane/methanol (9:1)).

Workup

  1. customthe suspension was evaporated down with silica gel
  2. customchromatographed with dichloromethane/methanol (97:3) on silica gel 70 at a flow rate of 30 mL/min
  3. customevaporated down to the residue
  4. dissolutiondissolved in dichloromethane
  5. filtrationfiltered
  6. distillationThe dichloromethane was distilled off
  7. customthe crystals formed
  8. filtrationwere suction filtered
  9. washwashed with diisopropyl ether

Sources & evidence

ORD record
ord-a598db9684da4d2b94d8573f8818fe8c
Source dataset
uspto-grants-2010_05
Patent number
US07723381B2

Reaction notes

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