2-[2-[3-Bromo-8-(4-morpholinyl)imidazo[1,2-b]pyridazin-2-yl]ethyl]quinoline → 1-(4-(8-Morpholino-2-(2-(quinolin-2-yl)ethyl)imidazo[1,2-b]pyridazin-3-yl)phenyl)-2-((2-(trimethylsilyl)ethoxy)methyl)-1,2-dihydro-1,2,4-triazol-3-one

HRID 718652Notes

Reaction equation

HRID 718652 reaction equation
Br[C:2]1[N:6]2[N:7]=[CH:8][CH:9]=[C:10]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)[C:5]2=[N:4][C:3]=1[CH2:17][CH2:18][C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]=1.CC1(C)C(C)(C)OB([C:37]2[CH:42]=[CH:41][C:40]([N:43]3[CH:47]=[N:46][C:45](=[O:48])[N:44]3[CH2:49][O:50][CH2:51][CH2:52][Si:53]([CH3:56])([CH3:55])[CH3:54])=[CH:39][CH:38]=2)O1>>[O:14]1[CH2:15][CH2:16][N:11]([C:10]2[C:5]3[N:6]([C:2]([C:37]4[CH:38]=[CH:39][C:40]([N:43]5[CH:47]=[N:46][C:45](=[O:48])[N:44]5[CH2:49][O:50][CH2:51][CH2:52][Si:53]([CH3:56])([CH3:55])[CH3:54])=[CH:41][CH:42]=4)=[C:3]([CH2:17][CH2:18][C:19]4[CH:28]=[CH:27][C:26]5[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=5)[N:20]=4)[N:4]=3)[N:7]=[CH:8][CH:9]=2)[CH2:12][CH2:13]1

Participants

3

Reactant 2

HCID 1177286942-[2-[3-Bromo-8-(4-morpholinyl)imidazo[1,2-b]pyridazin-2-yl]ethyl]quinolineHCID 1235782711-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-2-[[2-(trimethylsilyl)ethoxy]methyl]-2,3-dihydro-1H-1,2,4-triazol-3-one

Product 1

HCID 1231449431-(4-(8-Morpholino-2-(2-(quinolin-2-yl)ethyl)imidazo[1,2-b]pyridazin-3-yl)phenyl)-2-((2-(trimethylsilyl)ethoxy)methyl)-1,2-dihydro-1,2,4-triazol-3-one

Procedure

Compound 46a was subjected to Suzuki coupling conditions with compound 52d using the procedures described in Example 38, step A, to obtain compound 52e as a white solid. Mass Spectrum (LCMS, ESI pos.) Calcd. For C34H39N9O3Si: 649.3 (M+H). Found 649.2.

Sources & evidence

ORD record
ord-a9150812108844829d63f049b008040e
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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