Guaiacol → HCID 22036550, compound

HRID 991630Notes

Reaction equation

HRID 991630 reaction equation
N(C(N(C)C)=O)=NC(N(C)C)=O.C(OC([N:20]1[CH2:25][CH2:24][N:23]([C:26]2[C:27]([O:32][CH2:33][CH2:34][OH:35])=[N:28][CH:29]=[CH:30][N:31]=2)[CH2:22][CH2:21]1)=O)(C)(C)C.[CH3:36][O:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.CN(C=O)C>[N:23]1([C:26]2[C:27]([O:32][CH2:33][CH2:34][O:35][C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=3[O:37][CH3:36])=[N:28][CH:29]=[CH:30][N:31]=2)[CH2:22][CH2:21][NH:20][CH2:25][CH2:24]1

Participants

7

Reactant 4

HCID 460GuaiacolHCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 11776TriphenylphosphineHCID 114160742-[3-(4-Tert-butoxycarbonyl-1-piperazinyl)-2-pyrazinyloxy]ethanol

Product 1

HCID 22036550HCID 22036550, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

1,1′-Azobis(N,N-dimethylformamide) (TMAD; 60 mg, 0.35 mmol) was dissolved in THF (1 mL) and DMF (0.5 mL) and added to a stirred solution of the product from Step 2 (100 mg, 0.31 mmol), 2-methoxyphenol (124 mg, 1.00 mmol) and triphenylphosphine (92 mg, 0.35 mmol) in THF (1 mL). The reaction mixture was stirred for 15 h and then concentrated under reduced pressure. The residue was passed through a bed of silica gel using toluene/EtOAc/MeOH (45:45:10) as eluent, and the pure fractions were combined, concentrated and treated with CH2Cl2/TFA/H2O (50:45:5; 5 mL) for 30 min. The mixture was concentrated and the residue was purified by chromatography on silica gel using EtOAc/HOAc/MeOH/H2O (20:3:3:2) as eluent. The combined product-containing fractions were concentrated and partitioned between 5% aqueous NaOH and CH2Cl2. The organic phase was concentrated, and the residue was purified by chromatography on silica gel using CH2Cl2/MeOH (8:2) as eluent to give 11.2 mg (11%) of the title product. HRMS m/z calcd for C17H22N4O3 (M)+ 330.1692, found 330.1707.

Workup

  1. concentrationconcentrated under reduced pressure
  2. concentrationconcentrated
  3. additiontreated with CH2Cl2/TFA/H2O (50:45:5; 5 mL) for 30 min
  4. concentrationThe mixture was concentrated
  5. customthe residue was purified by chromatography on silica gel
  6. additionThe combined product-containing fractions
  7. concentrationwere concentrated
  8. custompartitioned between 5% aqueous NaOH and CH2Cl2
  9. concentrationThe organic phase was concentrated
  10. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-54a4f9aff17040c0b986ce64273679e6
Source dataset
uspto-grants-2002_10
Patent number
US06465467B1

Reaction notes

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