Pyridine → HCID 86728310, compound

HRID 1776932Notes

Reaction equation

HRID 1776932 reaction equation
[NH2:1][C:2]1[C:21]([C:22]2[CH:23]=[CH:24][C:25]3[O:38][CH2:37][N:28]4[C:29]5[CH:30]=[CH:31][CH:32]=[C:33]([F:36])[C:34]=5[CH:35]=[C:27]4[C:26]=3[N:39]=2)=[CH:20][C:5]2[C:6]([C:16]([NH:18][CH3:19])=[O:17])=[C:7]([C:9]3[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=3)[O:8][C:4]=2[CH:3]=1.N1C=CC=CC=1.[CH3:46][S:47](Cl)(=[O:49])=[O:48]>ClCCl>[F:36][C:33]1[C:34]2[CH:35]=[C:27]3[C:26]4[N:39]=[C:22]([C:21]5[C:2]([NH:1][S:47]([CH3:46])(=[O:49])=[O:48])=[CH:3][C:4]6[O:8][C:7]([C:9]7[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=7)=[C:6]([C:16]([NH:18][CH3:19])=[O:17])[C:5]=6[CH:20]=5)[CH:23]=[CH:24][C:25]=4[O:38][CH2:37][N:28]3[C:29]=2[CH:30]=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 86728298HCID 86728298, compound

Product 1

HCID 86728310HCID 86728310, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 6-amino-5-(11-fluoro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indol-2-yl)-2-(4-fluorophenyl)-N-methylbenzofuran-3-carboxamide (1000 mg, 1.914 mmol) and pyridine (1.548 mL, 19.14 mmol) in dichloromethane (30 mL), methylsulfonyl chloride (0.741 mL, 9.57 mmol) was added dropwise at 0° C. The mixture was allowed to room temperature and stirred overnight. The reaction mixture was quenched with NaHCO3 and 20 mL dichloromethane was added. Solid crushed out, the mixture was filtered and washed with water. The crude solid was dried under vacuum and gave the crude product 5-(11-fluoro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indol-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(methylsulfonamido)benzofuran-3-carboxamide (1100 mg, 96% yield).

Workup

  1. additionwas added dropwise at 0° C
  2. customwas allowed to room temperature
  3. customThe reaction mixture was quenched with NaHCO3 and 20 mL dichloromethane
  4. additionwas added
  5. customSolid crushed out
  6. filtrationthe mixture was filtered
  7. washwashed with water
  8. customThe crude solid was dried under vacuum

Sources & evidence

ORD record
ord-543e74d89e29472bbf06387b60362dd0
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

Loading…