4-(3-Bromo-2-(quinolin-2-ylethynyl)imidazo[1,2-b]pyridazin-8-yl)morpholine → (S)-tert-Butyl 3-methyl-2-(4-(8-morpholino-2-(quinolin-2-ylethynyl)imidazo[1,2-b]pyridazin-3-yl)benzamido)butanoate

HRID 718637Notes

Reaction equation

HRID 718637 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[C:17]#[C: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.[CH3:29][CH:30]([CH3:57])[C@H:31]([NH:39][C:40](=[O:56])[C:41]1[CH:46]=[CH:45][C:44](B2OC(C)(C)C(C)(C)O2)=[CH:43][CH:42]=1)[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33]>>[CH3:29][CH:30]([CH3:57])[C@H:31]([NH:39][C:40](=[O:56])[C:41]1[CH:42]=[CH:43][C:44]([C:2]2[N:6]3[N:7]=[CH:8][CH:9]=[C:10]([N:11]4[CH2:16][CH2:15][O:14][CH2:13][CH2:12]4)[C:5]3=[N:4][C:3]=2[C:17]#[C:18][C:19]2[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]=2)=[CH:45][CH:46]=1)[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33]

Participants

3

Reactant 2

HCID 1177283744-(3-Bromo-2-(quinolin-2-ylethynyl)imidazo[1,2-b]pyridazin-8-yl)morpholineHCID 123812944(S)-tert-Butyl 3-methyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamido)butanoate

Product 1

HCID 117732500(S)-tert-Butyl 3-methyl-2-(4-(8-morpholino-2-(quinolin-2-ylethynyl)imidazo[1,2-b]pyridazin-3-yl)benzamido)butanoate

Procedure

Compound 18b was subjected to Suzuki coupling conditions with compound 43a as described in Example 38, Step A to obtain compound 43b as a yellow solid. Mass Spectrum (LCMS, ESI pos.): Calcd. for C32H38N6O4: 631.3 (M+H). Found: 631.0.

Sources & evidence

ORD record
ord-b65b542d3df940708e2f91c23990ec91
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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