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Potassium Carbonate → 6-bromo-4-(((3S,4S)-1-(5-cyanopyridin-2-yl)-4-methylpyrrolidin-3-yl)amino)pyrrolo[1,2-b]pyridazine-3-carboxamide

HRID 877762
Notes
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Reaction equation

HRID 877762 reaction equation
I.[Br:2][C:3]1[CH:4]=[C:5]2[C:10]([NH:11][C@H:12]3[C@@H:16]([CH3:17])[CH2:15][NH:14][CH2:13]3)=[C:9]([C:18]([NH2:20])=[O:19])[CH:8]=[N:7][N:6]2[CH:21]=1.Br[C:23]1[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][N:24]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Br:2][C:3]1[CH:4]=[C:5]2[C:10]([NH:11][C@H:12]3[C@@H:16]([CH3:17])[CH2:15][N:14]([C:23]4[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][N:24]=4)[CH2:13]3)=[C:9]([C:18]([NH2:20])=[O:19])[CH:8]=[N:7][N:6]2[CH:21]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 50057186-Bromopyridine-3-carbonitrileHCID 682912146-bromo-4-(((3S,4S)-4-methylpyrrolidin-3-yl)amino)pyrrolo[1,2-b]pyridazine-3-carboxamide hydroiodide

Product 1

HCID 682913406-bromo-4-(((3S,4S)-1-(5-cyanopyridin-2-yl)-4-methylpyrrolidin-3-yl)amino)pyrrolo[1,2-b]pyridazine-3-carboxamideYield 97%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

A solution of 6-bromo-4-(((3S,4S)-4-methylpyrrolidin-3-yl)amino)pyrrolo[1,2-b]pyridazine-3-carboxamide hydroiodide (250 mg, 0.536 mmol), 6-bromonicotinonitrile (103 mg, 0.563 mmol) and potassium carbonate (222 mg, 1.609 mmol) in N,N-dimethylformamide (3 mL) was heated at 100° C. in a sealed tube for 90 min. The resulting mixture was cooled to room temperature, triturated with water and filtered. The filter cake was washed with water and dried under vacuum to give 6-bromo-4-(((3S,4S)-1-(5-cyanopyridin-2-yl)-4-methylpyrrolidin-3-yl)amino)pyrrolo[1,2-b]pyridazine-3-carboxamide (0.228 g, 97% yield). 1H NMR (400 MHz, 1:1 mixture of chloroform-d/methanol-d4) δ ppm 8.39-8.27 (m, 1H), 8.08 (s, 1H), 7.69-7.57 (m, 2H), 6.95-6.82 (m, 1H), 6.48 (d, J=9.0 Hz, 1H), 4.83 (br. s., 1H), 4.01-3.69 (m, 3H), 3.39 (t, J=9.6 Hz, 1H), 2.81 (br. s., 1H), 1.27 (d, J=6.8 Hz, 3H); MS (ES+) m/z: 440.2 (M+H); LC retention time: 3.885 min (analytical HPLC Method H).

Workup

  1. customtriturated with water
  2. filtrationfiltered
  3. washThe filter cake was washed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-ff981488784240b49e5747bfce976432
Source dataset
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08987268B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes