Water → HCID 44229842, compound

HRID 1969489Notes

Reaction equation

HRID 1969489 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:14]=[CH:13][NH:12][N:11]=2)[C:5]([C:15]#[N:16])=[C:4]([S:17][CH2:18][C:19]2[N:20]=[C:21]([C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=3)[S:22][CH:23]=2)[N:3]=1.C1CCN2C(=NCCC2)CC1.I[CH2:43][CH2:44][CH2:45][OH:46].O>CN(C=O)C.C(OCC)(=O)C>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:14]=[CH:13][N:12]([CH2:43][CH2:44][CH2:45][OH:46])[N:11]=2)[C:5]([C:15]#[N:16])=[C:4]([S:17][CH2:18][C:19]2[N:20]=[C:21]([C:24]3[CH:25]=[CH:26][C:27]([Cl:30])=[CH:28][CH:29]=3)[S:22][CH:23]=2)[N:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 693903-Iodo-1-propanolHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 178510466HCID 178510466, compound

Product 1

HCID 44229842HCID 44229842, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

50 mg (0.092 mmol) of the compound from Example 5 were dissolved in 0.8 ml of DMF, 15 mg (0.101 mmol) of DBU and 21 mg (0.111 mmol) of 3-iodopropanol were added and the mixture was stirred at 120° C. overnight. A little water and ethyl acetate were added to the mixture, and the two phases formed were separated. The aqueous phase was extracted twice with ethyl acetate. The combined organic phases were concentrated on a rotary evaporator and the residue was purified by thick-layer chromatography (toluene:acetonitrile=3:1).

Workup

  1. customthe two phases formed
  2. customwere separated
  3. extractionThe aqueous phase was extracted twice with ethyl acetate
  4. concentrationThe combined organic phases were concentrated on a rotary evaporator
  5. customthe residue was purified by thick-layer chromatography (toluene:acetonitrile=3:1)

Sources & evidence

ORD record
ord-642226e825314f368a65e4e4a49e15bc
Source dataset
uspto-grants-2013_04
Patent number
US08426602B2

Reaction notes

Loading…