Acetic Acid → HCID 90054867, compound

HRID 1772889Notes

Reaction equation

HRID 1772889 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][N:6]=[C:5]([NH:11][S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N+:21]([O-])=O)(=[O:14])=[O:13])[N:4]=1.[C:24](O)(=[O:26])C.C(N1C=CN=C1)(N1C=CN=C1)=O.C(N(CC)CC)C>CN(C=O)C.[Fe]>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][N:6]=[C:5]([N:11]2[C:24](=[O:26])[NH:21][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[S:12]2(=[O:14])=[O:13])[N:4]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 90023121HCID 90023121, compound

Product 1

HCID 90054867HCID 90054867, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared in two steps from N-(4,5-dimethoxypyrimidin-2-yl)-2-nitrobenzenesulfonamide (231 mg, 0.68 mmol), Fe powder (380 mg, 6.8 mmol) and acetic acid (5 mL); followed by 1,1′-carbonyldiimidazole (396 mg, 2.44 mmol) and triethylamine (0.17 mL, 1.22 mmol) in DMF (4.0 mL) using the methods of (IntA17), step 2 and (IntA14), step 3. The residue from step 3 was triturated with Et2O to yield the title compound (104 mg, 0.31 mmol).

Workup

  1. customThe residue from step 3 was triturated with Et2O

Sources & evidence

ORD record
ord-0db71ea8dc514b0dabba61ea01046350
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

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