Trifluoroacetic acid → N-{3-[3-(Aminomethyl)phenyl]-2,6-dimethylthieno[2,3-b]pyridin-4-yl}-3-chlorobenzenesulfonamide

HRID 573643Notes

Reaction equation

HRID 573643 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:8]([NH:11][C:12]2[CH:17]=[C:16]([CH3:18])[N:15]=[C:14]3[S:19][C:20]([CH3:37])=[C:21]([C:22]4[CH:23]=[C:24]([CH2:28][NH:29]C(=O)OC(C)(C)C)[CH:25]=[CH:26][CH:27]=4)[C:13]=23)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:29][CH2:28][C:24]1[CH:23]=[C:22]([C:21]2[C:13]3[C:14](=[N:15][C:16]([CH3:18])=[CH:17][C:12]=3[NH:11][S:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)(=[O:9])=[O:10])[S:19][C:20]=2[CH3:37])[CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68324039HCID 68324039, compound

Product 1

HCID 68323904N-{3-[3-(Aminomethyl)phenyl]-2,6-dimethylthieno[2,3-b]pyridin-4-yl}-3-chlorobenzenesulfonamideYield 8.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl {[3-(4-{[(3-chlorophenyl)sulfonyl]amino}-2,6-dimethylthieno[2,3-b]pyridin-3-yl)phenyl]methyl}carbamate (Example 70) (40 mg, 0.072 mmol) in DCM (2 mL) was added TFA (0.276 mL, 3.58 mmol) and the mixture stirred for 1 h. The mixture was then loaded onto an SCX cartridge and flushed with MeOH (3×5 mL) followed by 2M NH3 in MeOH (3×5 mL). The desired fractions were combined and concentrated and further purified by normal phase chromatography, eluting with a gradient of 0-20% 2M NH3 in MeOH in DCM, to give the title compound (2.8 mg). LCMS (A) m/z: 458 [M+1]+, Rt 0.96 min (basic).

Workup

  1. customflushed with MeOH (3×5 mL)
  2. concentrationconcentrated
  3. customfurther purified by normal phase chromatography
  4. washeluting with a gradient of 0-20% 2M NH3 in MeOH in DCM

Sources & evidence

ORD record
ord-91d880a71a14470f83a565597fe1ff4e
Source dataset
uspto-grants-2015_05
Patent number
US09029545B2

Reaction notes

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