Hydrochloric Acid → HCID 86756090, compound

HRID 1274616Notes

Reaction equation

HRID 1274616 reaction equation
[CH3:1][N:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5](=[O:12])[N:4]([C:13]2[C:14]([F:34])=[CH:15][C:16]3[O:20][N:19]=[C:18]([C:21]4[CH:26]=[C:25]([O:27][CH2:28][C:29](O)=[O:30])[CH:24]=[CH:23][C:22]=4[CH3:32])[C:17]=3[CH:33]=2)[C:3]1=[O:35].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:48][S:49]([NH2:52])(=[O:51])=[O:50].N1(C2CCCCCCCCCC2)CCCCCCCCCN1.Cl>O1CCCC1>[CH3:1][N:2]1[C:7]([C:8]([F:10])([F:11])[F:9])=[CH:6][C:5](=[O:12])[N:4]([C:13]2[C:14]([F:34])=[CH:15][C:16]3[O:20][N:19]=[C:18]([C:21]4[CH:26]=[C:25]([O:27][CH2:28][C:29]([NH:52][S:49]([CH3:48])(=[O:51])=[O:50])=[O:30])[CH:24]=[CH:23][C:22]=4[CH3:32])[C:17]=3[CH:33]=2)[C:3]1=[O:35]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 72879MethanesulfonamideHCID 57346892DiazabicycloundecaneHCID 70100356HCID 70100356, compound

Product 1

HCID 86756090HCID 86756090, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of {{2-{5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-6-fluoro-1,2-benzisoxazol-3-yl}-p-tolyl}oxy}acetic acid (1.54 g, 0.00312 mol) in tetrahydrofuran is added dropwise to a suspension of 1,1'-carbonyldiimidazole (1.06 g, 0.00655 mol) in tetrahydrofuran. The resultant mixture is stirred 1.5 hours and cooled to room temperature. A mixture of methanesulfonamide (0.594 g, 0.00624 mol), diazabicycloundecane (1.09 g, 0.00702 mol) and tetrahydrofuran is added dropwise. The resultant mixture is stirred overnight at room temperature and poured into 10% hydrochloric acid. The resultant white solid is filtered and dried to give the title compound (1.65 g, 91.6%, mp 123-125° C.) which is identified by NMR spectral analysis.

Workup

  1. additionis added dropwise
  2. filtrationThe resultant white solid is filtered
  3. customdried

Sources & evidence

ORD record
ord-4febe38b54ea46c78e96bedd1d00501d
Source dataset
uspto-grants-2000_12
Patent number
US06156700

Reaction notes

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