Trifluoroacetic acid → HCID 68328601, compound

HRID 634167Notes

Reaction equation

HRID 634167 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[N:12]=[C:11]([C:13]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([C:22]5[S:23][CH:24]=[N:25][N:26]=5)[CH:20]=4)[N:15](C(OC(C)(C)C)=O)[CH:14]=3)[CH:10]=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[S:23]1[CH:24]=[N:25][N:26]=[C:22]1[C:19]1[CH:20]=[C:21]2[C:16](=[CH:17][CH:18]=1)[NH:15][CH:14]=[C:13]2[C:11]1[N:12]=[C:7]([N:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68328156HCID 68328156, compound

Product 1

HCID 68328601HCID 68328601, compoundYield 50.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-(6-morpholinopyridin-2-yl)-5-(1,3,4-thiadiazol-2-yl)-1H-indole-1-carboxylate (86.0 mg, 0.186 mmol) in DCM (1.0 mL) was added TFA (1.0 mL) and the reaction was stirred at RT for 1 h, then solvent was removed. The residue was diluted with DCM (60 mL) and washed with sat. NaHCO3, dried, filtered and concentrated. The residue was purified with RP-HPLC to give 4-(6-(5-(1,3,4-thiadiazol-2-yl)-1H-indol-3-yl)pyridin-2-yl)morpholine (34.0 mg, 0.094 mmol, 50.4%) as a yellow solid. MS (ESI, pos. ion) m/z: 364 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.78 (1H, br. s.), 9.52 (1H, s), 9.17 (1H, d, J=1.4 Hz), 8.16 (1H, d, J=2.5 Hz), 7.92 (1H, dd, J=8.6, 1.6 Hz), 7.53-7.65 (2H, m), 7.24 (1H, d, J=7.6 Hz), 6.66 (1H, d, J=8.4 Hz), 3.78-3.90 (4H, m), 3.57-3.69 (4H, m).

Workup

  1. customsolvent was removed
  2. additionThe residue was diluted with DCM (60 mL)
  3. washwashed with sat. NaHCO3
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified with RP-HPLC

Sources & evidence

ORD record
ord-5e3a1d560a454d91883516485abcf383
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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