Morpholine → HCID 178508602, compound

HRID 2053002Notes

Reaction equation

HRID 2053002 reaction equation
[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:12]=3)=[CH:9][N:8]([C@H:25]3[CH2:28][C@H:27]([CH2:29][NH:30][C:31]([NH:33][CH2:34][CH2:35]Br)=[O:32])[CH2:26]3)[C:4]=2[N:5]=[CH:6][N:7]=1.BrCCN=C=O.[NH:43]1[CH2:48][CH2:47][O:46][CH2:45][CH2:44]1>C(O)C>[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:12]=3)=[CH:9][N:8]([C@H:25]3[CH2:28][C@H:27]([CH2:29][NH:30][C:31]([NH:33][CH2:34][CH2:35][N:43]4[CH2:48][CH2:47][O:46][CH2:45][CH2:44]4)=[O:32])[CH2:26]3)[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 42559572-Bromoethyl isocyanateHCID 178508601HCID 178508601, compound

Product 1

HCID 178508602HCID 178508602, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 41 mg (0.075 mmol) of trans-{3-[4-amino-5-(3-benzyloxy-phenyl)-pyrrolo[2,3-d]pyrimidin-7-yl]-cyclobutylmethyl}-3-(2-bromo-ethyl)-urea, which is prepared as described in Example 26 using 2-bromoethyl isocyanate (Aldrich, Buchs, Switzerland), in 5 ml of ethanol is added 33 μl (0.375 mmol) of morpholine. The mixture is refluxed for 3 h and the crude mixture is purified by medium-pressure liquid chromatography to provide trans-1-{3-[4-amino-5-(3-benzyloxy-phenyl)-pyrrolo[2,3-d]pyrimidin-7-yl]-cyclobutylmethyl}-3-(2-morpholin-4-yl-ethyl)-urea. Analytical HPLC: tR=6.12 min (Grad 2); ES-MS: m/eo=555.9.

Workup

  1. temperatureThe mixture is refluxed for 3 h
  2. customthe crude mixture is purified by medium-pressure liquid chromatography

Sources & evidence

ORD record
ord-cedd398ec866415ca8d31957ef297e43
Source dataset
uspto-grants-2008_02
Patent number
US07326699B2

Reaction notes

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