Oxalyl chloride → 3-azido-N-(5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-benzamide

HRID 2109175Notes

Reaction equation

HRID 2109175 reaction equation
[N:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[CH3:13])[C:7]([OH:9])=O)=[N+:2]=[N-:3].C(Cl)(=O)C(Cl)=O.[NH2:20][C:21]1[C:22]([O:36][CH3:37])=[C:23]([NH:31][S:32]([CH3:35])(=[O:34])=[O:33])[CH:24]=[C:25]([C:27]([CH3:30])([CH3:29])[CH3:28])[CH:26]=1.CCN(C(C)C)C(C)C>C(Cl)Cl.C1COCC1.CN(C=O)C>[N:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[CH3:13])[C:7]([NH:20][C:21]1[CH:26]=[C:25]([C:27]([CH3:29])([CH3:30])[CH3:28])[CH:24]=[C:23]([NH:31][S:32]([CH3:35])(=[O:34])=[O:33])[C:22]=1[O:36][CH3:37])=[O:9])=[N+:2]=[N-:3]

Participants

8

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 10214710N-(3-amino-5-tert-butyl-2-methoxy-phenyl)-methanesulfonamideHCID 179730913-Azido-4-methylbenzoic acid

Product 1

HCID 210792023-azido-N-(5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-benzamideYield 94.2%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

3-Azido-4-methyl benzoic acid (240 mg, 1.24 mmoL) was suspeneded in 3 mL of CH2Cl2 and 3 mL of THF. Oxalyl choride (0.14 mL, 1.5 mmol) was added, followed by 1 drop of 10% DMF in THF. The mixture was stirred for 1 h and then concentrated. The residue was redissolved in dry CH2Cl2 (5 mL) and 391 mg (1.27 mmol) of N-(3-amino-5-tert-butyl-2-methoxy-phenyl)-methane-sulfonamide was added followed by 0.4 ml (2.5 mmol) of DIPEA. The mixture became homogeneous, and was stirred for 4 h, and then was washed with 1M NaHSO4 and saturated NaHCO3. The washes were extracted once with CH2Cl2 and the extracts were combined, dried with Na2SO4, filtered, and concentrated to provide 516 mg (93%) of 3-azido-N-(5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-benzamide as a tan powder.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was redissolved in dry CH2Cl2 (5 mL)
  3. stirringwas stirred for 4 h
  4. washwas washed with 1M NaHSO4 and saturated NaHCO3
  5. extractionThe washes were extracted once with CH2Cl2
  6. dry with materialdried with Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-c4e5de2b32124397b8766b19f5540269
Source dataset
uspto-grants-2009_04
Patent number
US07514458B2

Reaction notes

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