Tributyltin azide → HCID 68291523, compound

HRID 877742Notes

Reaction equation

HRID 877742 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10]([NH:11][C@@H:12]3[CH2:23][C@@H:15]4[CH2:16][N:17]([S:19]([CH3:22])(=[O:21])=[O:20])[CH2:18][C@@H:14]4[C@H:13]3[CH3:24])=[C:9]([C:25]([NH2:27])=[O:26])[CH:8]=[N:7][N:6]2[CH:28]=1)#[N:2].[N:29]([Sn](CCCC)(CCCC)CCCC)=[N+:30]=[N-:31]>CN1CCCC1=O>[CH3:24][C@@H:13]1[C@@H:14]2[C@@H:15]([CH2:16][N:17]([S:19]([CH3:22])(=[O:20])=[O:21])[CH2:18]2)[CH2:23][C@H:12]1[NH:11][C:10]1[C:5]2[N:6]([CH:28]=[C:3]([C:1]3[N:29]=[N:30][NH:31][N:2]=3)[CH:4]=2)[N:7]=[CH:8][C:9]=1[C:25]([NH2:27])=[O:26]

Participants

4

Reactant 2

HCID 4984872Tributyltin azideHCID 68291574HCID 68291574, compound

Product 1

HCID 68291523HCID 68291523, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 6-cyano-4-(((3aS,4R,5R,6aS)-4-methyl-2-(methylsulfonyl)octahydrocyclopenta[c]pyrrol-5-yl)amino)pyrrolo[1,2-b]pyridazine-3-carboxamide (34 mg, 0.084 mmol) and azidotributyltin (0.028 mL, 0.101 mmol) in 1-methyl-2-pyrrolidinone (1 mL) was heated to 180° C. under microwave for 1 h. LCMS analysis showed that the expected product was observed as the major peak. The reaction mixture was taken to the next step without purification. MS (ES+) m/z: 446.1 (M+H).

Sources & evidence

ORD record
ord-fc0414598fd44081b15288f214e3a62f
Source dataset
uspto-grants-2015_03
Patent number
US08987268B2

Reaction notes

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