HCID 59619981, compound → HCID 59619812, compound

HRID 445705Notes

Reaction equation

HRID 445705 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.[Cl:25][C:26]1[C:31]([NH:32][CH2:33][CH3:34])=[CH:30][C:29](B2OC(C)(C)C(C)(C)O2)=[CH:28][N:27]=1>>[Cl:25][C:26]1[N:27]=[CH:28][C:29]([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:30][C:31]=1[NH:32][CH2:33][CH3:34]

Participants

3

Reactant 2

HCID 59619981HCID 59619981, compound2×HCID 59620024HCID 59620024, compound

Product 1

HCID 59619812HCID 59619812, 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, 0.101 mmol) and [2-chloro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-3-yl]-ethyl-amine (stage 153.1.1) to give the title compound as a yellow solid. (HPLC: tR 2.74 min (Method A); M+H=462 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 8.99 (s, 1H), 8.13-8.08 (m, 1H), 7.98-7.93 (m, 1H), 7.76-7.73 (m, 1H), 7.58-7.54 (m, 1H), 6.97-6.93 (m, 1H), 5.72 (t, 1H), 3.79 (s, 3H), 3.59 (s, 3H), 3.26 (qt, 2H), 2.07 (s, 3H), 1.91 (s, 3H), 1.22 (t, 3H))

Workup

  1. customThe title compound was synthesized in a similar manner

Sources & evidence

ORD record
ord-9f6f31b4137a463c915fc0c7bc30d726
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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