HCID 59619981, compound → HCID 59620051, compound

HRID 445706Notes

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.[CH2:25]([NH:27][C:28]1[C:29]([F:43])=[N:30][CH:31]=[C:32](B2OC(C)(C)C(C)(C)O2)[CH:33]=1)[CH3:26]>>[CH2:25]([NH:27][C:28]1[CH:33]=[C:32]([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:31]=[N:30][C:29]=1[F:43])[CH3:26]

Participants

Reactant 2

HCID 59619981HCID 59619981, compound2×

HCID 59620019HCID 59620019, compound

Product 1

HCID 59620051HCID 59620051, 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, 0.104 mmol) and ethyl-[2-fluoro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-3-yl]-amine (stage 154.1.1) to give the title compound as a white solid. (HPLC: tR 2.63 min (Method A); M+H=446 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 8.97 (s, 1H), 8.11-8.07 (m, 1H), 7.96-7.91 (m, 1H), 7.55-7.52 (m, 1H), 7.48-7.45 (m, 1H), 7.00-6.95 (m, 1H), 5.96 (t, 1H), 3.78 (s, 3H), 3.59 (s, 3H), 3.20 (qt, 2H), 2.07 (s, 3H), 1.91 (s, 3H), 1.23 (t, 3H))

Workup

customThe title compound was synthesized in a similar manner

Sources & evidence

ORD record: ord-9767d352f9ee4405a4f2ebf0a7c0516e
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08476294B2

Reaction notes

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