Dimethylformamide → HCID 86671461, compound

HRID 1530505Notes

Reaction equation

HRID 1530505 reaction equation
[CH:1]([N:4]1[C:8]([C:9]2[N:18]=[C:17]3[N:11]([CH2:12][CH2:13][O:14][C:15]4[CH:22]=[CH:21][C:20]([S:23]([OH:26])(=O)=[O:24])=[CH:19][C:16]=43)[CH:10]=2)=[N:7][CH:6]=[N:5]1)([CH3:3])[CH3:2].C(Cl)(=O)C([Cl:30])=O.CN(C=O)C>C1COCC1>[CH:1]([N:4]1[C:8]([C:9]2[N:18]=[C:17]3[N:11]([CH2:12][CH2:13][O:14][C:15]4[CH:22]=[CH:21][C:20]([S:23]([Cl:30])(=[O:26])=[O:24])=[CH:19][C:16]=43)[CH:10]=2)=[N:7][CH:6]=[N:5]1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 86671460HCID 86671460, compound

Product 1

HCID 86671461HCID 86671461, compoundYield 208.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulene-9-sulfonic acid (228 mg, 0.61 mmol) in THF (15 mL) was added oxalyl chloride (257 μL, 3.04 mmol) and the resulting mixture stirred at RT for 15 min. The reaction mixture was cooled to 0° before DMF (126 μL, 1.69 mmol) was added and the resulting mixture warmed to RT after 10 min then stirred for a further 2 h. The reaction mixture was azeotroped with toluene affording 2-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulene-9-sulfonyl chloride (500 mg).

Workup

  1. additionwas added
  2. temperaturethe resulting mixture warmed to RT after 10 min
  3. stirringthen stirred for a further 2 h
  4. customThe reaction mixture was azeotroped with toluene

Sources & evidence

ORD record
ord-f7cf4368f58044648f1adff371999c51
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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