Diisopropylethylamine → HCID 68350414, compound

HRID 877835Notes

Reaction equation

HRID 877835 reaction equation
I.[Br:2][C:3]1[CH:4]=[C:5]2[C:10]([NH:11][C@H:12]3[C@:16]([F: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].CCN(C(C)C)C(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C)C=O.C(OCC)(=O)C>[Br:2][C:3]1[CH:4]=[C:5]2[C:10]([NH:11][C@H:12]3[C@:16]([F:18])([CH3:17])[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

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 27332591-Cyanocyclopropanecarboxylic acidHCID 68291912HCID 68291912, compound

Product 1

HCID 68350414HCID 68350414, compoundYield 75.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 6-bromo-4-(((3R,4S)-4-fluoro-4-methylpyrrolidin-3-yl)amino)pyrrolo[1,2-b]pyridazine-3-carboxamide hydroiodide (100 mg, 0.207 mmol), 1-cyanocyclopropanecarboxylic acid (27.5 mg, 0.248 mmol), Hunig's base (0.144 mL, 0.826 mmol) and BOP (110 mg, 0.248 mmol) in N,N-dimethylformamide (2 mL) was stirred at room temperature for 2 h. The resulting mixture was diluted with ethyl acetate (80 mL) and washed with saturated NaHCO3, water, brine, dried (MgSO4) and concentrated to give crude 6-bromo-4-(((3R,4S)-1-(1-cyanocyclopropanecarbonyl)-4-fluoro-4-methylpyrrolidin-3-yl)amino)pyrrolo[1,2-b]pyridazine-3-carboxamide (70 mg), which was taken to the next step without purification. MS (ES+) m/z: 449.0 (M+H).

Workup

  1. washwashed with saturated NaHCO3, water, brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-11c047b1dce8473a80d46e2e22960f9c
Source dataset
uspto-grants-2015_03
Patent number
US08987268B2

Reaction notes

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