Methanol → Luminespib

HRID 2097294Notes

Reaction equation

HRID 2097294 reaction equation
[CH2:1]([NH:3][C:4]([C:6]1[C:10]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[CH:13][CH:12]=2)=[C:9]([C:24]2[CH:29]=[C:28]([CH:30]([CH3:32])[CH3:31])[C:27]([O:33]CC3C=CC=CC=3)=[CH:26][C:25]=2[O:41]CC2C=CC=CC=2)[O:8][N:7]=1)=[O:5])[CH3:2].CO>C(Cl)Cl>[CH2:1]([NH:3][C:4]([C:6]1[C:10]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[CH:13][CH:12]=2)=[C:9]([C:24]2[CH:29]=[C:28]([CH:30]([CH3:31])[CH3:32])[C:27]([OH:33])=[CH:26][C:25]=2[OH:41])[O:8][N:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 887MethanolHCID 247736255-(2,4-bis(benzyloxy)-5-isopropylphenyl)-N-ethyl-4-(4-(morpholinomethyl)phenyl)isoxazole-3-carboxamide

Product 1

HCID 135539077Luminespib

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5-(2,4-Bis-benzyloxy-5-isopropyl-phenyl)-4-(4-morpholin-4-ylmethyl-phenyl)-isoxazole-3-carboxylic acid ethylamide (1 eq) was dissolved in an. DCM and under a nitrogen atmosphere, was cooled to 0° C. 1MBCl3 in DCM was added drop wise and the solution was stirred under these conditions for 30 minutes. Methanol (2 ml) was added and the reaction mixture was concentrated in vacuo. Purification of the sample by preparative LC/MS gave 5-(2,4-dihydroxy-5-isopropyl-phenyl)-4-(4-morpholin-4-ylmethyl-phenyl)-isoxazole-3-carboxylic acid ethylamide as a white solid.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customPurification of the sample by preparative LC/MS

Sources & evidence

ORD record
ord-89d58bf86c3446359d0eddc0ceaf97e2
Source dataset
uspto-grants-2013_05
Patent number
US08450310B2

Reaction notes

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