2-(4-Aminophenyl)-7-(2-morpholin-4-yl-ethoxy)imidazo[2,1-b]-[1,3]benzothiazole → HCID 46214308, compound

HRID 1038318Notes

Reaction equation

HRID 1038318 reaction equation
[OH:1][CH2:2][C:3]([C:7]1[O:11][N:10]=[C:9]([NH:12][C:13](=[O:21])OC2C=CC=CC=2)[CH:8]=1)([CH3:6])[CH2:4][OH:5].[N:22]1([CH2:28][CH2:29][O:30][C:31]2[CH:49]=[CH:48][C:34]3[N:35]4[CH:40]=[C:39]([C:41]5[CH:46]=[CH:45][C:44]([NH2:47])=[CH:43][CH:42]=5)[N:38]=[C:36]4[S:37][C:33]=3[CH:32]=2)[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1>CN(C)C1C=CN=CC=1.C1COCC1>[OH:5][CH2:4][C:3]([C:7]1[O:11][N:10]=[C:9]([NH:12][C:13]([NH:47][C:44]2[CH:43]=[CH:42][C:41]([C:39]3[N:38]=[C:36]4[N:35]([CH:40]=3)[C:34]3[CH:48]=[CH:49][C:31]([O:30][CH2:29][CH2:28][N:22]5[CH2:23][CH2:24][O:25][CH2:26][CH2:27]5)=[CH:32][C:33]=3[S:37]4)=[CH:46][CH:45]=2)=[O:21])[CH:8]=1)([CH2:2][OH:1])[CH3:6]

Participants

5

Reactant 2

HCID 445986692-(4-Aminophenyl)-7-(2-morpholin-4-yl-ethoxy)imidazo[2,1-b]-[1,3]benzothiazoleHCID 66794001HCID 66794001, compound

Product 1

HCID 46214308HCID 46214308, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of phenyl 5-(1,3-dihydroxy-2-methylpropan-2-yl)isoxazol-3-ylcarbamate (1 equivalent), 7-(2-morpholin-4-yl-ethoxy)-2-(4-aminophenyl)imidazo[2,1-b]benzothiazole (4) (1 equivalent) and 4-(dimethylamino)pyridine (0.05-0.5 equivalents) in anhydrous THF is stirred at a temperature between rt and 50° C. until the reaction is substantially complete as monitored by LCMS or TLC. The mixture is concentrated under reduced pressure and the residue is purified by preparative reverse-phase HPLC or silica gel flash chromatography to afford 1-[5-(2-hydroxy-1-hydroxymethyl-1-methyl-ethyl)-isoxazol-3-yl]-3-{4-[7-(2-morpholin-4-yl-ethoxy)-benzo[d]imidazo[2,1-b]thiazol-2-yl]-phenyl}-urea (I-1a).

Workup

  1. concentrationThe mixture is concentrated under reduced pressure
  2. customthe residue is purified by preparative reverse-phase HPLC or silica gel flash chromatography

Sources & evidence

ORD record
ord-8c004b14ef92401fa3b169294c9e567e
Source dataset
uspto-grants-2013_10
Patent number
US08551963B2

Reaction notes

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