Trifluoroacetic acid → HCID 178477651, compound

HRID 1671652Notes

Reaction equation

HRID 1671652 reaction equation
N([O-])=O.[Na+].FC(F)(F)C(O)=O.[CH2:12]([S:14]([C:17]1[CH:44]=[CH:43][C:20]([O:21][C:22]2[C:23]([CH:37]3[O:41][CH:40]([OH:42])[CH2:39][CH2:38]3)=[CH:24][C:25]3[N:29]=[C:28]([C:30]4[CH:35]=[N:34][CH:33]=[CH:32][N:31]=4)[NH:27][C:26]=3[CH:36]=2)=[CH:19][CH:18]=1)(=[O:16])=[O:15])[CH3:13]>>[CH2:12]([S:14]([C:17]1[CH:44]=[CH:43][C:20]([O:21][C:22]2[C:23]([CH:37]3[O:41][C:40](=[O:42])[CH2:39][CH2:38]3)=[CH:24][C:25]3[N:29]=[C:28]([C:30]4[CH:35]=[N:34][CH:33]=[CH:32][N:31]=4)[NH:27][C:26]=3[CH:36]=2)=[CH:19][CH:18]=1)(=[O:15])=[O:16])[CH3:13]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 23668193Sodium NitriteHCID 178477652HCID 178477652, compound

Product 1

HCID 178477651HCID 178477651, compound

Procedure

Sodium nitrite (5 mg) was added to a trifluoroacetic acid (1 ml) solution of 5-(6-(4-(ethylsulfonyl)phenoxy)-2-pyrazin-2-yl-1H-benzimidazol-5-yl)tetrahydrofuran-2-ol (3.3 mg) obtained in Example 9, and the reaction liquid was stirred at room temperature for 10 minutes. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through reversed-phase middle-pressure liquid chromatography (ODS-AS-360-CC (by YMC), mobile phase: water/acetonitrile/0.1% trifluoroacetic acid), and the resulting fraction was diluted with ethyl acetate, washed with aqueous saturated sodium bicarbonate and saturated saline water in that order, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure to obtain the entitled compound as a yellow foamy substance.

Workup

  1. customthe reaction liquid
  2. customThe solvent was evaporated away under reduced pressure
  3. customthe resulting residue was purified through reversed-phase middle-pressure liquid chromatography (ODS-AS-360-CC (by YMC), mobile phase: water/acetonitrile/0.1% trifluoroacetic acid)
  4. additionthe resulting fraction was diluted with ethyl acetate
  5. washwashed with aqueous saturated sodium bicarbonate and saturated saline water in that order
  6. dry with materialdried with anhydrous sodium sulfate
  7. customThe solvent was evaporated away under reduced pressure
  8. customto obtain the entitled compound as a yellow foamy substance

Sources & evidence

ORD record
ord-8c66ffc6b94344319c32cd58d09ddf72
Source dataset
uspto-grants-2011_08
Patent number
US07994331B2

Reaction notes

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