Dimethylformamide → HCID 68291185, compound

HRID 877817Notes

Reaction equation

HRID 877817 reaction equation
[CH3:1][C:2]1([CH3:27])[CH2:6][NH:5][CH2:4][CH:3]1[NH:7][C:8]1[C:9]2[N:10]([CH:17]=[C:18](C3C=NN(CC)C=3)[CH:19]=2)[N:11]=[CH:12][C:13]=1[C:14]([NH2:16])=[O:15].Br[C:29]1[CH:36]=[CH:35][C:32]([C:33]#[N:34])=[CH:31][N:30]=1.CC[N:39]([CH:43]([CH3:45])C)[CH:40]([CH3:42])C.[CH3:46][N:47](C=O)C>>[C:33]([C:32]1[CH:35]=[CH:36][C:29]([N:5]2[CH2:6][C:2]([CH3:27])([CH3:1])[CH:3]([NH:7][C:8]3[C:9]4[N:10]([CH:17]=[C:18]([C:46]5[CH:45]=[CH:43][N:39]([CH2:40][CH3:42])[N:47]=5)[CH:19]=4)[N:11]=[CH:12][C:13]=3[C:14]([NH2:16])=[O:15])[CH2:4]2)=[N:30][CH:31]=1)#[N:34]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 50057186-Bromopyridine-3-carbonitrileHCID 68292271HCID 68292271, compound

Product 1

HCID 68291185HCID 68291185, compoundYield 2%

Conditions

Temperature
100 °C

Procedure

To a solution of 4-((4,4-dimethylpyrrolidin-3-yl)amino)-6-(1-ethyl-1H-pyrazol-4-yl)pyrrolo[1,2-b]pyridazine-3-carboxamide (38 mg, 0.103 mmol) in DMF (0.3 mL), was added 6-bromonicotinonitrile (20.8 mg, 0.114 mmol), DIPEA (0.06 mL, 0.31 mmol), The mixture was heated at 100° C. overnight. The reaction was cooled to rt, and purified via preparative HPLC to afford 15 mg of the. The product was subjected to chiral SFC chromatography to afford the title compound (1.1 mg, 2% yield) as a single enantiomer. 1H NMR (400 MHz, METHANOL-d4) δ 8.40 (d, J=1.8 Hz, 1H), 8.16 (s, 1H), 8.02 (s, 1H), 7.87-7.83 (m, 2H), 7.76 (dd, J=8.9, 2.3 Hz, 1H), 7.21 (d, J=1.8 Hz, 1H), 6.65 (d, J=8.8 Hz, 1H), 4.22 (q, J=7.3 Hz, 2H), 3.70-3.54 (m, 3H), 3.51-3.49 (m, 1H), 3.18-3.14 (m, 1H), 1.51 (t, J=7.3 Hz, 3H), 1.32 (d, J=9.7 Hz, 6H). MS (ES+) m/z: 470.32 (M+H); LC retention time: 3.50 min (analytical HPLC Method H).

Workup

  1. temperatureThe reaction was cooled to rt
  2. custompurified via preparative HPLC
  3. customto afford 15 mg of the

Sources & evidence

ORD record
ord-56ec6146a43b403f920a6948fe663bfd
Source dataset
uspto-grants-2015_03
Patent number
US08987268B2

Reaction notes

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