Trimethylsilyl iodide → HCID 68291496, compound

HRID 877821Notes

Reaction equation

HRID 877821 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9]([NH:10][C@H:11]3[C@@H:15]([O:16][CH3:17])[CH2:14][N:13](C(OCC4C=CC=CC=4)=O)[CH2:12]3)=[C:8]([C:28](=[O:30])[NH2:29])[CH:7]=[N:6][N:5]2[CH:31]=1.I[Si](C)(C)C>C(#N)C.CCOCC>[Br:1][C:2]1[CH:3]=[C:4]2[C:9]([NH:10][C@H:11]3[C@@H:15]([O:16][CH3:17])[CH2:14][NH:13][CH2:12]3)=[C:8]([C:28]([NH2:29])=[O:30])[CH:7]=[N:6][N:5]2[CH:31]=1

Participants

5

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 68350400HCID 68350400, compound

Product 1

HCID 68291496HCID 68291496, compoundYield 135.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of (3R,4S)-benzyl 3-((6-bromo-3-carbamoylpyrrolo[1,2-b]pyridazin-4-yl)amino)-4-methoxypyrrolidine-1-carboxylate (300 mg, 0.61 mmol) in acetonitrile (5 mL), was added iodotrimethylsilane (123 mg, 0.614 mmol) at 0° C., the mixture was then stirred at rt for 2 h. The mixture was diluted with ether (30 mL), stirred for 1 h, filtered and rinsed with ether to give the hydroiodide salt of 6-bromo-4-(((3R,4S)-4-methoxypyrrolidin-3-yl)amino)pyrrolo[1,2-b]pyridazine-3-carboxamide (292 mg, 99% yield) as a brown solid. 1H NMR (400 MHz, METHANOL-d4) δ 8.17 (s, 1H), 7.70 (d, J=1.5 Hz, 1H), 7.07 (s, 1H), 4.97-4.88 (m, 2H), 4.56 (br. s., 1H), 4.16-4.09 (m, 1H), 3.67 (dd, J=11.4, 7.7 Hz, 1H), 3.53-3.50 (m, 3H), 3.50-3.45 (m, 1H), 3.40-3.34 (m, 1H), 3.11 (dd, J=11.6, 8.5 Hz, 1H); MS (ES+) m/z: 353.1, 354.0 (M+H); LC retention time: 2.01 min (analytical HPLC Method B).

Workup

  1. stirringstirred for 1 h
  2. filtrationfiltered
  3. washrinsed with ether

Sources & evidence

ORD record
ord-5104f59f12f642ec9e400bec5a94e760
Source dataset
uspto-grants-2015_03
Patent number
US08987268B2

Reaction notes

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