Morpholine → HCID 178515409, compound

HRID 1158635Notes

Reaction equation

HRID 1158635 reaction equation
Br[C:2]1[N:11]=[C:10]([C:12]2[NH:16][C:15]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)=[N:14][N:13]=2)[C:9]([OH:25])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1>>[F:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][C:15]2[NH:16][C:12]([C:10]3[C:9]([OH:25])=[C:8]4[C:3]([CH:4]=[CH:5][CH:6]=[N:7]4)=[C:2]([N:26]4[CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)[N:11]=3)=[N:13][N:14]=2)=[CH:19][CH:20]=1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 178515407HCID 178515407, compound

Product 1

HCID 178515409HCID 178515409, compoundYield 55%

Procedure

A solution of 5-bromo-7-[5-(4-fluorobenzyl)-4H-1,2,4-triazol-3-yl]-1,6-naphthyridin-8-ol (34 mg, 0.09 mmol) in neat morpholine was heated in a sealed tube at 150° C. for 16 hours. The excess amine was removed in vacuo and the residue purified by preparative HPLC to provide the title compound (19 mg, 55%) as a white solid. 1H NMR (CDCl3): δ 9.14 (dd, J=4.4, 1.6 Hz, 1 H), 8.45 (dd, J=8.4, 1.6 Hz, 1 H), 7.57 (dd, J=8.4, 4.4 Hz, 1 H), 7.36 (dd, J=8.4, 5.2 Hz, 2 H), 7.01 (t, J=8.4 Hz, 2 H), 4.19 (s, 2 H), 3.98 (t, J=4.4 Hz, 4 H), 3.33 (t, J=4.4 Hz, 4 H); 13C NMR (CDCl3): δ 168.49, 161.79 (d, JCR=243.6 Hz), 154.85, 153.95, 153.40, 146.07, 144.75, 133.88, 132.99 (d, JCF=3.0 Hz), 130.40 (d, JCF=130.4 Hz), 122.67, 120.81, 119.70, 115.37 (d, JCF=21.2 Hz), 66.88, 52.06, 33.71; MS m/z 407 (M+1).

Workup

  1. customThe excess amine was removed in vacuo
  2. customthe residue purified by preparative HPLC

Sources & evidence

ORD record
ord-679a3b0dc5224cf697e62faa937e72b6
Source dataset
uspto-grants-2010_10
Patent number
US07812016B2

Reaction notes

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