HCID 59613098, compound → HCID 59619913, compound

HRID 445694Notes

Reaction equation

Br[C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]([CH3:24])[C:13](=[O:23])[N:14]([C:15]4[C:16]([CH3:22])=[N:17][N:18]([CH3:21])[C:19]=4[CH3:20])[C:5]=3[C:4]=2[CH:3]=1.[F:25][C:26]1[C:27]([NH:41][CH3:42])=[N:28][CH:29]=[C:30](B2OC(C)(C)C(C)(C)O2)[CH:31]=1>>[F:25][C:26]1[CH:31]=[C:30]([C:2]2[CH:11]=[CH:10][C:9]3[N:8]=[CH:7][C:6]4[N:12]([CH3:24])[C:13](=[O:23])[N:14]([C:15]5[C:16]([CH3:22])=[N:17][N:18]([CH3:21])[C:19]=5[CH3:20])[C:5]=4[C:4]=3[CH:3]=2)[CH:29]=[N:28][C:27]=1[NH:41][CH3:42]

Participants

Reactant 2

HCID 59613098HCID 59613098, compound

HCID 59619981HCID 59619981, compound2×

Product 1

HCID 59619913HCID 59619913, compound

Procedure

The title compound was synthesized in a similar manner as described for Example 1.1 using 8-bromo-3-methyl-1-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1,3-dihydro-imidazo[4,5-c]quinolin-2-one (Intermediate H) and [3-fluoro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-2-yl]-methyl-amine (stage 141.1.1) to give the title compound as a yellow foam. (HPLC: tR 2.15 min (Method A); M+H=432 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 8.92 (s, 1H), 8.05-7.99 (m, 2H), 7.89-7.84 (m, 1H), 7.41-7.36 (m, 1H), 7.35-7.33 (m, 1H), 6.92-6.86 (m, 1H), 3.83 (s, 3H), 3.58 (s, 3H), 2.88 (d, 3H), 2.07 (s, 3H), 1.91 (s, 3H))

Workup

customThe title compound was synthesized in a similar manner

Sources & evidence

ORD record: ord-fac69c9ed6ac4b3bad9d627fac5bb138
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08476294B2

Reaction notes

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