Diisopropylethylamine → 6-Bromo-4-((1-(1-cyanocyclopropanecarbonyl)-4,4-dimethylpyrrolidin-3-yl)amino)pyrrolo[1,2-b]pyridazine-3-carboxamide

HRID 877812Notes

Reaction equation

HRID 877812 reaction equation
I.[Br:2][C:3]1[CH:4]=[C:5]2[C:10]([NH:11][CH:12]3[C:16]([CH3:18])([CH3:17])[CH2:15][NH:14][CH2:13]3)=[C:9]([C:19]([NH2:21])=[O:20])[CH:8]=[N:7][N:6]2[CH:22]=1.[C:23]([C:25]1([C:28](O)=[O:29])[CH2:27][CH2:26]1)#[N:24].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C>CN(C=O)C>[Br:2][C:3]1[CH:4]=[C:5]2[C:10]([NH:11][CH:12]3[C:16]([CH3:17])([CH3:18])[CH2:15][N:14]([C:28]([C:25]4([C:23]#[N:24])[CH2:27][CH2:26]4)=[O:29])[CH2:13]3)=[C:9]([C:19]([NH2:21])=[O:20])[CH:8]=[N:7][N:6]2[CH:22]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 27332591-Cyanocyclopropanecarboxylic acidHCID 682920786-Bromo-4-((4,4-dimethylpyrrolidin-3-yl)amino)pyrrolo[1,2-b]pyridazine-3-carboxamide hydroiodide

Product 1

HCID 682916676-Bromo-4-((1-(1-cyanocyclopropanecarbonyl)-4,4-dimethylpyrrolidin-3-yl)amino)pyrrolo[1,2-b]pyridazine-3-carboxamideYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (+/−)-6-bromo-4-((4,4-dimethylpyrrolidin-3-yl)amino)pyrrolo[1,2-b]pyridazine-3-carboxamide hydroiodide (50 mg, 0.104 mmol) in DMF (0.3 mL), was added 1-cyanocyclopropanecarboxylic acid (13.9 mg, 0.13 mmol), BOP (55.4 mg, 0.13 mmol), DIPEA (0.046 mL, 0.26 mmol). The mixture was stirred at rt for 3 h, quenched with water then filtered. The solid was rinsed with water, dried under vacuum to give 6-bromo-4-((1-(1-cyanocyclopropanecarbonyl)-4,4-dimethylpyrrolidin-3-yl)amino)pyrrolo[1,2-b]pyridazine-3-carboxamide (36 mg, 78% yield) was obtained as a brown solid. MS (ES+) m/z: 444.1, 445.2 (M+H).

Workup

  1. customquenched with water
  2. filtrationthen filtered
  3. washThe solid was rinsed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-6a867d23c2d24d2bb9a200cc370722dc
Source dataset
uspto-grants-2015_03
Patent number
US08987268B2

Reaction notes

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