6-Chloro-4-morpholinopyridazin-3-amine → 4-(6-Chloro-2-((1R,2S)-2-(quinolin-2-yl)cyclopropyl)imidazo[1,2-b]pyridazin-8-yl)morpholine

HRID 718706Notes

Reaction equation

HRID 718706 reaction equation
Br[CH2:2][C:3]([C@@H:5]1[CH2:7][C@@H:6]1[C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1)=O.[Cl:18][C:19]1[N:24]=[N:23][C:22]([NH2:25])=[C:21]([N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[CH:20]=1>CN(C=O)C.C(Cl)Cl>[Cl:18][C:19]1[CH:20]=[C:21]([N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[C:22]2[N:23]([CH:2]=[C:3]([C@@H:5]3[CH2:7][C@@H:6]3[C:8]3[CH:17]=[CH:16][C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[N:9]=3)[N:25]=2)[N:24]=1

Participants

5

Reactant 2

HCID 575175366-Chloro-4-morpholinopyridazin-3-amineHCID 1177284202-Bromo-1-((1R,2S)-2-(quinolin-2-yl)cyclopropyl)ethanone

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Compound 79c (67 mg, 0.23 mmol) was dissolved in DMF (2 mL) and compound 19a (50 mg, 0.23 mmol) was added in one portion. The reaction was allowed to stir for 48 h under an argon atmosphere, at which time it was diluted with DCM (50 mL) and washed with saturated sodium bicarbonate (50 mL). The organic layer was concentrated under reduced pressure and then purified by preparative TLC (5% MeOH/DCM) to afford compound 79d. Mass spectrum (LCMS, ESI pos.) Calcd. For C22H20ClN5O 406.1 (M+H). found 406.2.

Workup

  1. washwashed with saturated sodium bicarbonate (50 mL)
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. custompurified by preparative TLC (5% MeOH/DCM)

Sources & evidence

ORD record
ord-143be76bcc134a47ac6d756f2adaad6d
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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