Toluene → 6-bromo-3-[(1S,2S)-2-hydroxycyclohexyl]-10-methyl-7,8,9,10-tetrahydropyrido[3,2-h]quinazolin-4(3H)-one

HRID 925624Notes

Reaction equation

HRID 925624 reaction equation
[NH2:1][C:2]1[C:3]([C:14]([NH:16][C@H:17]2[CH2:22][CH2:21][CH2:20][CH2:19][C@@H:18]2[OH:23])=[O:15])=[CH:4][C:5]([Br:13])=[C:6]2[C:11]=1[N:10]([CH3:12])[CH2:9][CH2:8][CH2:7]2.[C:24]1(C)C=CC=CC=1>CN(C(OC)OC)C>[Br:13][C:5]1[CH:4]=[C:3]2[C:2](=[C:11]3[N:10]([CH3:12])[CH2:9][CH2:8][CH2:7][C:6]=13)[N:1]=[CH:24][N:16]([C@H:17]1[CH2:22][CH2:21][CH2:20][CH2:19][C@@H:18]1[OH:23])[C:14]2=[O:15]

Participants

4

Reactant 2

HCID 1140TolueneHCID 892160708-amino-5-bromo-N-[(1S,2S)-2-hydroxycyclohexyl]-1-methyl-1,2,3,4-tetrahydroquinoline-7-carboxamide

Product 1

HCID 710421236-bromo-3-[(1S,2S)-2-hydroxycyclohexyl]-10-methyl-7,8,9,10-tetrahydropyrido[3,2-h]quinazolin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 78373Dimethylformamide dimethyl acetalSolvent

Procedure

A solution of 8-amino-5-bromo-N-[(1S,2S)-2-hydroxycyclohexyl]-1-methyl-1,2,3,4-tetrahydroquinoline-7-carboxamide (758 mg, 1.98 mmol) in toluene (6 mL) and DMF-DMA (5.3 mL) was heated in a sealed tube at 135° C. for 3 h. The resulting mixture was concentrated and purified by silica gel chromatography (0-4% MeOH/CH2Cl2) to afford 6-bromo-3-[(1S,2S)-2-hydroxycyclohexyl]-10-methyl-7,8,9,10-tetrahydropyrido[3,2-h]quinazolin-4(3H)-one in pure form.

Workup

  1. concentrationThe resulting mixture was concentrated
  2. custompurified by silica gel chromatography (0-4% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-14cdc714be5e4758b9cf172bcef866a4
Source dataset
uspto-grants-2016_03
Patent number
US09284312B2

Reaction notes

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