2-(4-Aminophenyl)-7-(2-morpholin-4-yl-ethoxy)imidazo[2,1-b]-[1,3]benzothiazole → HCID 46214309, compound

HRID 1038323Notes

Reaction equation

HRID 1038323 reaction equation
[OH:1][CH2:2][C:3]([C:8]1[O:12][N:11]=[C:10]([NH:13][C:14](=[O:22])OC2C=CC=CC=2)[CH:9]=1)([CH2:6][OH:7])[CH2:4][OH:5].[N:23]1([CH2:29][CH2:30][O:31][C:32]2[CH:50]=[CH:49][C:35]3[N:36]4[CH:41]=[C:40]([C:42]5[CH:47]=[CH:46][C:45]([NH2:48])=[CH:44][CH:43]=5)[N:39]=[C:37]4[S:38][C:34]=3[CH:33]=2)[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1>CN(C)C1C=CN=CC=1.C1COCC1>[OH:7][CH2:6][C:3]([C:8]1[O:12][N:11]=[C:10]([NH:13][C:14]([NH:48][C:45]2[CH:44]=[CH:43][C:42]([C:40]3[N:39]=[C:37]4[N:36]([CH:41]=3)[C:35]3[CH:49]=[CH:50][C:32]([O:31][CH2:30][CH2:29][N:23]5[CH2:24][CH2:25][O:26][CH2:27][CH2:28]5)=[CH:33][C:34]=3[S:38]4)=[CH:47][CH:46]=2)=[O:22])[CH:9]=1)([CH2:2][OH:1])[CH2:4][OH:5]

Participants

5

Reactant 2

HCID 445986692-(4-Aminophenyl)-7-(2-morpholin-4-yl-ethoxy)imidazo[2,1-b]-[1,3]benzothiazoleHCID 66794313HCID 66794313, compound

Product 1

HCID 46214309HCID 46214309, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of phenyl 5-(1,3-dihydroxy-2-(hydroxymethyl)propan-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 reaction mixture is concentrated under reduced pressure and the residue is purified by either preparative reverse-phase HPLC or silica gel flash chromatography to afford 1-[5-(2-hydroxy-1,1-bis-hydroxymethyl-ethyl)-isoxazol-3-yl]-3-{4-[7-(2-morpholin-4-yl-ethoxy)-benzo[d]imidazo[2,1-b]thiazol-2-yl]-phenyl}-urea (I-1b).

Workup

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

Sources & evidence

ORD record
ord-489e550b4448444989163a6c8cfa42bb
Source dataset
uspto-grants-2013_10
Patent number
US08551963B2

Reaction notes

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