Trifluoroacetic acid → HCID 178474073, compound

HRID 2402093Notes

Reaction equation

HRID 2402093 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:10]2[C:11]([C:36]#[N:37])=[C:12]([C:26]3[CH:31]=[CH:30][N:29]=[C:28]([NH:32][C:33](=[O:35])[CH3:34])[CH:27]=3)[S:13][C:14]=2[C:15]2[N:19]=[CH:18][N:17](C3CCCCO3)[N:16]=2)=[O:9])=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:10]2[C:11]([C:36]#[N:37])=[C:12]([C:26]3[CH:31]=[CH:30][N:29]=[C:28]([NH:32][C:33](=[O:35])[CH3:34])[CH:27]=3)[S:13][C:14]=2[C:15]2[NH:19][CH:18]=[N:17][N:16]=2)=[O:9])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68006866HCID 68006866, compound

Product 1

HCID 178474073HCID 178474073, compoundYield 41.9%

Procedure

N-(4-(4-(4-chlorophenylsulfinyl)-3-cyano-5-(1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl)thiophen-2-yl)pyridin-2-yl)acetamide (0.0315 g, 0.0570 mmol) was dissolved in TFA (5.00 mL, 64.9 mmol). The mixture was stirred at room temperature for 1 hr, and the solvent was evaporated. 10 ml DCM was added to redissolve the material followed by the addition of triethylamine (1 mL). The solvent was evaporated off, and the mixture was purified by silica gel column. The eluent was 0-6% methanol in hexane to yield a solid product (0.0112 g, yield 41.9%) LCMS: (AA) ES+ 469, 471. 1H NMR (300 MHz, MeOD) δ: 8.65 (s, 1H), 8.51 (s, 1H), 8.42 (d, 1H), 8.06 (d, 2H), 7.58 (d, 2H), 7.44 (dd, 1H), 2.25 (s, 3H).

Workup

  1. customthe solvent was evaporated
  2. addition10 ml DCM was added
  3. dissolutionto redissolve the material
  4. additionfollowed by the addition of triethylamine (1 mL)
  5. customThe solvent was evaporated off
  6. customthe mixture was purified by silica gel column

Sources & evidence

ORD record
ord-ce6c00a5d1384b9aae53f733901e4c58
Source dataset
uspto-grants-2014_08
Patent number
US08796271B2

Reaction notes

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