Methyl 2-(4-bromophenyl)acetate → Methyl 2-(4-(6-chloro-8-morpholino-2-((1R,25)-2-(quinolin-2-yl)cyclopropyl)imidazo[1,2-b]pyridazin-3-yl)phenyl)acetate

HRID 718710Notes

Reaction equation

HRID 718710 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[C:5]2[N:6]([CH:8]=[C:9]([C@@H:11]3[CH2:13][C@@H:12]3[C:14]3[CH:23]=[CH:22][C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[N:15]=3)[N:10]=2)[N:7]=1.Br[C:31]1[CH:36]=[CH:35][C:34]([CH2:37][C:38]([O:40][CH3:41])=[O:39])=[CH:33][CH:32]=1>>[Cl:1][C:2]1[CH:3]=[C:4]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[C:5]2[N:6]([C:8]([C:31]3[CH:36]=[CH:35][C:34]([CH2:37][C:38]([O:40][CH3:41])=[O:39])=[CH:33][CH:32]=3)=[C:9]([C@@H:11]3[CH2:13][C@@H:12]3[C:14]3[CH:23]=[CH:22][C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[N:15]=3)[N:10]=2)[N:7]=1

Participants

3

Reactant 2

HCID 316783Methyl 2-(4-bromophenyl)acetateHCID 1177284914-(6-Chloro-2-((1R,2S)-2-(quinolin-2-yl)cyclopropyl)imidazo[1,2-b]pyridazin-8-yl)morpholine

Product 1

HCID 131734184Methyl 2-(4-(6-chloro-8-morpholino-2-((1R,25)-2-(quinolin-2-yl)cyclopropyl)imidazo[1,2-b]pyridazin-3-yl)phenyl)acetate

Procedure

Compound 79d (60 mg, 0.14 mmol) was coupled with methyl 2-(4-bromophenyl)acetate (46 μL, 0.22 mmol) using the procedures described in Example 20, Step A to afford compound 82a. Mass Spectrum (LCMS, ESI pos.): Calcd. for C31H28ClN5O3: 554.2 (M+H). found: 544.2.

Sources & evidence

ORD record
ord-bbddaa1ebb5b4812bbfe186a1b272673
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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