HCID 59612882, compound → HCID 59620083, compound

HRID 445747Notes

Reaction equation

HRID 445747 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]([CH3:33])[C:13](=[O:32])[N:14]([C:15]4[C:16]([CH3:31])=[N:17][N:18]([CH2:21][CH2:22][O:23][Si](C(C)(C)C)(C)C)[C:19]=4[CH3:20])[C:5]=3[C:4]=2[CH:3]=1.[CH2:34]([NH:36][C:37]1[C:38]([CH3:52])=[N:39][CH:40]=[C:41](B2OC(C)(C)C(C)(C)O2)[CH:42]=1)[CH3:35]>>[CH2:34]([NH:36][C:37]1[CH:42]=[C:41]([C:2]2[CH:11]=[CH:10][C:9]3[N:8]=[CH:7][C:6]4[N:12]([CH3:33])[C:13](=[O:32])[N:14]([C:15]5[C:16]([CH3:31])=[N:17][N:18]([CH2:21][CH2:22][OH:23])[C:19]=5[CH3:20])[C:5]=4[C:4]=3[CH:3]=2)[CH:40]=[N:39][C:38]=1[CH3:52])[CH3:35]

Participants

3

Reactant 2

HCID 59612882HCID 59612882, compoundHCID 59619633HCID 59619633, compound

Product 1

HCID 59620083HCID 59620083, compound

Procedure

The title compound was synthesized in a similar manner as described for Example 1.1 using 8-Bromo-1-{1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3,5-dimethyl-1H-pyrazol-4-yl}-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one (stage 210.1.1) and ethyl-[2-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-3-yl]-amine (Stage 87.1.1) to give the title compound as an off-white solid; deprotection of the silyl group occurred during the purification step. (HPLC: tR 2.16 min (Method A); M+H=472 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 8.96 (s, 1H), 8.10-8.06 (m, 1H), 7.94-7.90 (m, 1H), 7.85-7.82 (m, 1H), 7.55-7.52 (m, 1H), 6.83-6.80 (m, 1H), 5.21 (t, 1H), 4.92 (t, 1H), 4.21-4.03 (m, 2H), 3.81-3.67 (m, 2H), 3.59 (s, 3H), 3.24-3.14 (m, 2H), 2.32 (s, 3H), 2.09 (s, 3H), 1.94 (s, 3H), 1.24 (t, 3H))

Workup

  1. customThe title compound was synthesized in a similar manner

Sources & evidence

ORD record
ord-e5bfa795bc0c4eaf8faeb6ce64bebe5d
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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