Ammonium Chloride → HCID 52915079, compound

HRID 1183529Notes

Reaction equation

HRID 1183529 reaction equation
[CH2:1]([N:8]1[CH:12]=[C:11]([CH:13]([OH:38])[C:14]2[C:15]([CH3:37])=[N:16][O:17][C:18]=2[C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][C:28]([C:31]4([C:34](O)=[O:35])[CH2:33][CH2:32]4)=[CH:27][CH:26]=3)=[CH:21][CH:20]=2)[N:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:51][S:52]([NH2:55])(=[O:54])=[O:53].C1CCN2C(=NCCC2)CC1.[NH4+].[Cl-]>C1COCC1.CCOC(C)=O.O>[CH2:1]([N:8]1[CH:12]=[C:11]([CH:13]([OH:38])[C:14]2[C:15]([CH3:37])=[N:16][O:17][C:18]=2[C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:26]=[CH:27][C:28]([C:31]4([C:34]([NH:55][S:52]([CH3:51])(=[O:54])=[O:53])=[O:35])[CH2:33][CH2:32]4)=[CH:29][CH:30]=3)=[CH:21][CH:20]=2)[N:10]=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

9

Reactant 5

HCID 25517Ammonium ChlorideHCID 682631,1'-CarbonyldiimidazoleHCID 72879MethanesulfonamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 66577536HCID 66577536, compound

Product 1

HCID 52915079HCID 52915079, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-(4′-{4-[(1-benzyl-1H-[1,2,3]triazol-4-yl)-hydroxy-methyl]-3-methyl-isoxazol-5-yl}-biphenyl-4-yl)-cyclopropanecarboxylic acid (Enantiomer B) (0.100 g, 0.197 mmol), carbonyldiimidazole (0.080 g, 0.5 mmol), N,N-dimethylamino pyridine (0.002 g, 0.02 mmol) in THF (2 mL) was stirred at room temperature overnight. Added MeSO2NH2 (0.050 g, 0.5 mmol) and DBU (0.100 mL, 0.65 mmol) and the mixture heated to 100° C. in a capped vial for 4.5 hours. The solution was poured into sat. aqueous NH4Cl, then water and EtOAc was added. The organic layer was separated, dried (Na2SO4), concentrated and the resulting reside purified by preparative HPLC to yield the title compound.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customthe resulting reside purified by preparative HPLC

Sources & evidence

ORD record
ord-7c7eb7886a4d4d629a5014aeaefd1875
Source dataset
uspto-grants-2014_03
Patent number
US08664220B2

Reaction notes

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