Water → HCID 18536259, compound

HRID 412014Notes

Reaction equation

HRID 412014 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:13]([NH:15][CH2:16][CH2:17][N:18]2[CH2:23][CH2:22][N:21]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([Cl:32])[CH:26]=3)[CH2:20][CH2:19]2)=[O:14])=[C:6]([CH:12]=1)[O:7][CH2:8][C:9](O)=[O:10].C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:45][CH:46]([CH3:49])[CH2:47][OH:48].O>CN(C)C=O.CCOCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:13]([NH:15][CH2:16][CH2:17][N:18]2[CH2:23][CH2:22][N:21]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([Cl:32])[CH:26]=3)[CH2:20][CH2:19]2)=[O:14])=[C:6]([O:7][CH2:8][C:9]([NH:45][CH:46]([CH3:49])[CH2:47][OH:48])=[O:10])[CH:12]=1

Participants

7

Reactant 4

HCID 962WaterHCID 51262-AminopropanolHCID 682631,1'-CarbonyldiimidazoleHCID 18536250HCID 18536250, compound

Product 1

HCID 18536259HCID 18536259, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

The product of Example 2 (0.3 g) was dissolved in N,N-dimethylformamide (3 ml). 1,1′-Carbonyldiimidazole (0.1 g) and 2-amino-1-propanol (5 molar equivalents) were added, the solution heated at 60° C. for 1.5 hours and cooled. Water and ether were added, the organic phase separated and concentrated to a gum which was purified by chromatography (dichloromethane:methanol, 9:1) to give the product as a solid (0.15 g), m.p. 115-116° C.

Workup

  1. temperaturecooled
  2. customthe organic phase separated
  3. concentrationconcentrated to a gum which
  4. customwas purified by chromatography (dichloromethane:methanol, 9:1)

Sources & evidence

ORD record
ord-9b9c26ca6c0d4068a2b897f7951f116b
Source dataset
uspto-grants-2003_05
Patent number
US06562825B1

Reaction notes

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