Isopropanol → HCID 135982082, compound

HRID 1161520Notes

Reaction equation

HRID 1161520 reaction equation
F[B-](F)(F)F.[F:6][C:7]1[C:12]2[CH2:13][O:14][CH2:15][O:16][C:11]=2[C:10]([O:17][CH3:18])=[CH:9][C:8]=1[CH:19]([NH:34][C:35]1[CH:40]=[CH:39][C:38]([C:41](=S)[NH2:42])=[CH:37][CH:36]=1)[C:20]1[NH:24][C:23](=[O:25])[N:22]([C:26]2[N:27]=[CH:28][S:29][C:30]=2[C:31]([NH2:33])=[O:32])[N:21]=1.C(O)(C)C.C[SiH](C)[NH:50][SiH](C)C>C(#N)C>[C:41]([C:38]1[CH:37]=[CH:36][C:35]([NH:34][CH:19]([C:8]2[CH:9]=[C:10]([O:17][CH3:18])[C:11]3[O:16][CH2:15][O:14][CH2:13][C:12]=3[C:7]=2[F:6])[C:20]2[NH:24][C:23](=[O:25])[N:22]([C:26]3[N:27]=[CH:28][S:29][C:30]=3[C:31]([NH2:33])=[O:32])[N:21]=2)=[CH:40][CH:39]=1)(=[NH:42])[NH2:50]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 26255TetrafluoroborateHCID 85196Silanamine, N-(dimethylsilyl)-1,1-dimethyl-HCID 135982163HCID 135982163, compound

Product 1

HCID 135982082HCID 135982082, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

After adding 33 mg of Me3O+BF4− to a suspension of 109 mg of 4-{3-[(5-fluoro-8-methoxy-4H-benzo[1,3]dioxin-6-yl)-(4-thiocarbamoylphenylamino)methyl]-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl}thiazole-5-carboxylic acid amide in 1 ml of acetonitrile, the mixture was stirred at room temperature for 30 minutes. Next, 4 ml of isopropanol and 0.055 ml of 1,1,3,3-tetramethyldisilazane were added to the reaction mixture, which was then stirred overnight at 60° C. The reaction mixture was concentrated, and the residue was purified by reverse-phase high performance liquid chromatography (acetonitrile-water, 0.1% acetic acid) to give 4-{3-[(4-carbamimidoylphenylamino)-(5-fluoro-8-methoxy-4H-benzo[1,3]dioxin-6-yl)methyl]-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl}thiazole-5-carboxylic acid amide (36 mg).

Workup

  1. stirringwas then stirred overnight at 60° C
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified by reverse-phase high performance liquid chromatography (acetonitrile-water, 0.1% acetic acid)

Sources & evidence

ORD record
ord-0bec8eac93744949be8f0e4f3a1fcd99
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

Loading…