8-Bromo-1-(1,3-dimethyl-1H-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one → HCID 59620000, compound

HRID 445614Notes

Reaction equation

HRID 445614 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]([CH3:23])[C:13](=[O:22])[N:14]([C:15]4[C:16]([CH3:21])=[N:17][N:18]([CH3:20])[CH:19]=4)[C:5]=3[C:4]=2[CH:3]=1.[CH2:24]([O:26][C:27]1[C:32]([N:33]([CH3:37])[C:34](=[O:36])[CH3:35])=[CH:31][C:30](B2OC(C)(C)C(C)(C)O2)=[CH:29][N:28]=1)[CH3:25]>>[CH3:20][N:18]1[CH:19]=[C:15]([N:14]2[C:5]3[C:4]4[CH:3]=[C:2]([C:30]5[CH:31]=[C:32]([N:33]([CH3:37])[C:34](=[O:36])[CH3:35])[C:27]([O:26][CH2:24][CH3:25])=[N:28][CH:29]=5)[CH:11]=[CH:10][C:9]=4[N:8]=[CH:7][C:6]=3[N:12]([CH3:23])[C:13]2=[O:22])[C:16]([CH3:21])=[N:17]1

Participants

3

Reactant 2

HCID 596197398-Bromo-1-(1,3-dimethyl-1H-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one2×HCID 59619757Acetamide, N-[2-ethoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinyl]-N-methyl-

Product 1

HCID 59620000HCID 59620000, compound

Procedure

The title compound was synthesized in a similar manner as described for Example 1.1 using 8-bromo-1-(1,3-dimethyl-1H-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one (Intermediate A) and N-[2-ethoxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-3-yl]-N-methyl-acetamide (Stage 63.1.1) to give the title compound as a white solid. (HPLC: tR 2.64 min (Method A); M+H=486 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 8.97 (s, 1H), 8.40-8.28 (m, 1H), 8.18-8.06 (m, 2H), 8.04-7.91 (m, 1H), 7.85-7.69 (m, 1H), 7.54-7.41 (m, 1H), 4.52-4.33 (m, 2H), 3.88 (s, 3H), 3.58 (s, 3H), 3.08 (s, 3H), 1.93 (s, 3H), 1.75 (s, 3H), 1.32 (t, 3H))

Workup

  1. customThe title compound was synthesized in a similar manner

Sources & evidence

ORD record
ord-e942896d78874161bbdf20adad3e6c1d
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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