Methanol → 8-bromo-1-[1-(2-hydroxy-ethyl)-3-methyl-1H-pyrazol-4-yl]-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one

HRID 445665Notes

Reaction equation

C[O:2][C:3](=O)[CH2:4][N:5]1[CH:9]=[C:8]([N:10]2[C:22]3[C:21]4[CH:20]=[C:19]([Br:23])[CH:18]=[CH:17][C:16]=4[N:15]=[CH:14][C:13]=3[N:12]([CH3:24])[C:11]2=[O:25])[C:7]([CH3:26])=[N:6]1.CO.[BH4-].[Na+]>C1COCC1>[Br:23][C:19]1[CH:18]=[CH:17][C:16]2[N:15]=[CH:14][C:13]3[N:12]([CH3:24])[C:11](=[O:25])[N:10]([C:8]4[C:7]([CH3:26])=[N:6][N:5]([CH2:4][CH2:3][OH:2])[CH:9]=4)[C:22]=3[C:21]=2[CH:20]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of [4-(8-bromo-3-methyl-2-oxo-2,3-dihydro-imidazo[4,5-c]quinolin-1-yl)-3-methyl-pyrazol-1-yl]-acetic acid methyl ester (Stage 101.1.1a, 60 mg, 0.139 mmol) and MeOH (0.021 ml, 0.519 mmol) in THF (1.5 ml) was cooled to 0° C. Then NaBH4 (14 mg, 0.370 mmol) was added and the RM was heated to 50° C. for 30 min. After that, the RM was quenched with saturated aqueous NaHCO3 (20 ml) and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and evaporated to dryness to give the title compound as a lightly yellow solid. (HPLC: tR 2.23 min (Method A); M+H=402, 404 Br-Pattern MS-ES)

Workup

temperaturethe RM was heated to 50° C. for 30 min
customAfter that, the RM was quenched with saturated aqueous NaHCO3 (20 ml)
extractionextracted with EtOAc (2×)
washThe combined organic layers were washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
customevaporated to dryness

Sources & evidence

ORD record: ord-56a1636249724c6b99736a90b2e27ce6
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08476294B2

Reaction notes

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