Trifluoroacetic acid → 3-Fluoro-4-(2-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)thieno[3,2-b]pyridin-7-yloxy)aniline

HRID 2193731Notes

Reaction equation

HRID 2193731 reaction equation
[C:1](O)([C:3](F)(F)F)=O.[F:8][C:9]1[CH:10]=[C:11]([NH:32]C(=O)OC(C)(C)C)[CH:12]=[CH:13][C:14]=1[O:15][C:16]1[CH:21]=[CH:20][N:19]=[C:18]2[CH:22]=[C:23](C3CN(C)CCC=3)[S:24][C:17]=12>>[F:8][C:9]1[CH:10]=[C:11]([CH:12]=[CH:13][C:14]=1[O:15][C:16]1[CH:21]=[CH:20][N:19]=[C:18]2[CH:22]=[C:23]([C:16]3[CH2:17][CH2:18][N:19]([CH3:20])[CH2:1][CH:3]=3)[S:24][C:17]=12)[NH2:32]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58790215Tert-butyl 3-fluoro-4-(2-(1-methyl-1,2,5,6-tetrahydropyridin-3-yl)thieno[3,2-b]pyridin-7-yloxy)phenylcarbamate

Product 1

HCID 167179683-Fluoro-4-(2-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)thieno[3,2-b]pyridin-7-yloxy)anilineYield 48%

Procedure

TFA (1 mL) was added to tert-butyl 3-fluoro-4-(2-(1-methyl-1,2,5,6-tetrahydropyridin-3-yl)thieno[3,2-b]pyridin-7-yloxy)phenylcarbamate (229) (105 mg, 0.23 mmol) and the mixture was stirred for 1 h at room temperature. The solution was concentrated under reduced pressure, the residue co-distilled with MeCN, redissolved in MeOH and purified by preparative HPLC (gradient 40% to 95% MeOH in water, 45 min) giving 230 (50 mg, 0.1 mmol, 48% yield) as a white solid. MS (m/z): (M+1) 356.1 (100%).

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. dissolutionthe residue co-distilled with MeCN, redissolved in MeOH
  3. custompurified by preparative HPLC (gradient 40% to 95% MeOH in water, 45 min)

Sources & evidence

ORD record
ord-77fd6f41bd3e4fbfa426936f165e4cc1
Source dataset
uspto-grants-2012_12
Patent number
US08329726B2

Reaction notes

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