Diphosgene → 8-bromo-1-(1,3-dimethyl-1H-pyrazol-4-yl)-1,3-dihydro-imidazo[4,5-c]quinolin-2-one

HRID 445537

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([NH2:12])=[C:5]2[NH:13][C:14]1[C:15]([CH3:20])=[N:16][N:17]([CH3:19])[CH:18]=1.Cl[C:22](OC(Cl)(Cl)Cl)=[O:23]>C(Cl)Cl>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[NH:12][C:22](=[O:23])[N:13]([C:14]4[C:15]([CH3:20])=[N:16][N:17]([CH3:19])[CH:18]=4)[C:5]=3[C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 6-bromo-N*4*-(1,3-dimethyl-1H-pyrazol-4-yl)-quinoline-3,4-diamine (Stage A.2, 3.15 g, 8.15 mmol) and TEA (1.36 ml, 9.79 mmol) in DCM (65 ml) was added under argon, after cooling with an ice-bath, a solution of trichloromethyl chloroformate (1.08 ml, 8.97 mmol in DCM (65 ml). The mixture was stirred for 25 min at 0° C. Then the RM was quenched with sat. aqueous NaHCO3 (300 ml) and 10 M aqueous NaOH (4 ml) and well stirred. The phases were separated and extracted with EtOAc (3×). The combined organic layers were washed with brine (2×), dried over Na2SO4, filtered and evaporated to dryness to give the title compound as a brownish solid (HPLC tR 2.29 min (Method A); M+H=360; M−H=358 MS-ES)

Workup

temperatureafter cooling with an ice-bath
customThen the RM was quenched with sat. aqueous NaHCO3 (300 ml) and 10 M aqueous NaOH (4 ml)
stirringwell stirred
customThe phases were separated
extractionextracted with EtOAc (3×)
washThe combined organic layers were washed with brine (2×)
dry with materialdried over Na2SO4
filtrationfiltered
customevaporated to dryness

Sources & evidence

ORD record: ord-246aaacf031e4a2598929e88d677f106
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08476294B2

Linked notes

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