Morpholine → HCID 178508596, compound

HRID 2053008Notes

Reaction equation

HRID 2053008 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]OS(C4C=CC(C)=CC=4)(=O)=O)[CH2:26]3)[C:4]=2[N:5]=[CH:6][N:7]=1.[NH:41]1[CH2:46][CH2:45][O:44][CH2:43][CH2:42]1>>[CH2:18]([O:17][C:13]1[CH:12]=[C:11]([C:10]2[C:3]3[C:2]([NH2:1])=[N:7][CH:6]=[N:5][C:4]=3[N:8]([C@H:25]3[CH2:28][C@H:27]([CH2:29][N:41]4[CH2:46][CH2:45][O:44][CH2:43][CH2:42]4)[CH2:26]3)[CH:9]=2)[CH:16]=[CH:15][CH:14]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 178427768HCID 178427768, compound

Product 1

HCID 178508596HCID 178508596, compound

Procedure

A solution of 50 mg (0.09 mmol) of trans-toluene-4-sulfonic acid 3-[4-amino-5-(3-benzyloxy-phenyl)-pyrrolo[2,3-d]pyrimidin-7-yl]-cyclobutylmethyl ester in 1 ml of morpholine (Fluka, Buchs, Switzerland) is stirred at RT for 72 h. The solvent is evaporated to dryness and the residue is purified by flash-chromatography (ethylacetate:methanol:NH4OHaqu.=95:5:1) to provide trans-5-(3-benzyloxy-phenyl)-7-(3-morpholin-4-ylmethyl-cyclobutyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine. Analytical HPLC: tR=9.29 min (Grad 1); ES-MS: m/eo=470.0.

Workup

  1. customThe solvent is evaporated to dryness
  2. customthe residue is purified by flash-chromatography (ethylacetate:methanol:NH4OHaqu.=95:5:1)

Sources & evidence

ORD record
ord-a69bb926fc4a42488b29edc03acf8d19
Source dataset
uspto-grants-2008_02
Patent number
US07326699B2

Reaction notes

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