tert-Butyl 4-bromo-2-fluorobenzoate → tert-butyl 4-(6-chloro-8-morpholino-2-((1R,2S)-2-(quinolin-2-yl)cyclopropyl)imidazo[1,2-b]pyridazin-3-yl)-2-fluorobenzoate

HRID 718708Notes

Reaction equation

HRID 718708 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:43]=[CH:42][C:34]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])=[C:33]([F:44])[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:43]=[CH:42][C:34]([C:35]([O:37][C:38]([CH3:41])([CH3:39])[CH3:40])=[O:36])=[C:33]([F:44])[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 46738774tert-Butyl 4-bromo-2-fluorobenzoateHCID 1177284914-(6-Chloro-2-((1R,2S)-2-(quinolin-2-yl)cyclopropyl)imidazo[1,2-b]pyridazin-8-yl)morpholine

Product 1

HCID 117728451tert-butyl 4-(6-chloro-8-morpholino-2-((1R,2S)-2-(quinolin-2-yl)cyclopropyl)imidazo[1,2-b]pyridazin-3-yl)-2-fluorobenzoate

Procedure

Compound 79d (100 mg, 0.246 mmol) was coupled with tert-butyl 4-bromo-2-fluorobenzoate (102 mg, 0.370 mmol) using the procedures described in Example 20, Step A to afford compound 81a. Mass Spectrum (LCMS, ESI pos.): Calcd. for C33H31ClFN5O3: 600.2 (M+H). found: 600.2.

Sources & evidence

ORD record
ord-b3c9682e89874e16a4cb94c3ee8391cc
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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