Morpholine → HCID 178425227, compound

HRID 1526980Notes

Reaction equation

HRID 1526980 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]2[C:10]([C:11]([NH:13][CH2:14][C:15]3[C:16]([OH:23])=[N:17][C:18]([CH3:22])=[CH:19][C:20]=3[CH3:21])=[O:12])=[C:9]([CH3:24])[N:8]([C@@H:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH3:26])[C:6]=2[N:7]=1.[NH:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1>>[OH:23][C:16]1[C:15]([CH2:14][NH:13][C:11]([C:10]2[C:5]3[CH:4]=[N:3][C:2]([N:33]4[CH2:38][CH2:37][O:36][CH2:35][CH2:34]4)=[N:7][C:6]=3[N:8]([C@@H:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH3:26])[C:9]=2[CH3:24])=[O:12])=[C:20]([CH3:21])[CH:19]=[C:18]([CH3:22])[N:17]=1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 178425225HCID 178425225, compound

Product 1

HCID 178425227HCID 178425227, compoundYield 70.5%

Procedure

A solution of (R)-2-chloro-N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-6-methyl-7-(1-phenylethyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide (70 mg, 0.15 mmol) in morpholine (1.0 mL) was stirred at 150° C. for 30 minutes under microwave (pressure: 10.5 bar, equipment power: 150 W). The mixture was concentrated in vacuo and purified by column chromatography (silica gel, dichloromethane/methanol=10:1) to afford (R)-N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-6-methyl-2-morpholino-7-(1-phenylethyl)-7H-pyrrolo[23-d]pyrimidine-5-carboxamide (55 mg, 70.5%). LRMS (M+H+) m/z: calcd 500.25. found 500. HPLC purity (214 nm): 98.6%. 1H NMR (400 MHz, CD3OD) δ 8.65 (s, 1H), 7.28 (dt, J=11.9, 7.7 Hz, 5H), 6.10 (dd, J=13.7, 6.5 Hz, 2H), 4.51 (s, 2H), 3.78-3.65 (m, 8H), 2.47 (s, 3H), 2.41 (s, 3H), 2.26 (s, 3H), 2.03 (d, J=7.2 Hz, 3H).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. custompurified by column chromatography (silica gel, dichloromethane/methanol=10:1)

Sources & evidence

ORD record
ord-42dc8c34d6484fd2a77c48cca0777d56
Source dataset
uspto-grants-2015_07
Patent number
US09085583B2

Reaction notes

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