HCID 68328327, compound → HCID 68328329, compound

HRID 634159Notes

Reaction equation

HRID 634159 reaction equation
[NH2:1][C:2]1[S:6][C:5]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[N:12](C(OC(C)(C)C)=O)[CH:11]=[C:10]3[C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)[N:24]=2)=[N:4][N:3]=1>C(Cl)Cl.C(O)(C(F)(F)F)=O>[O:32]1[CH2:31][CH2:30][N:29]([C:25]2[N:24]=[C:23]([C:10]3[C:9]4[C:13](=[CH:14][CH:15]=[C:7]([C:5]5[S:6][C:2]([NH2:1])=[N:3][N:4]=5)[CH:8]=4)[NH:12][CH:11]=3)[CH:28]=[CH:27][CH:26]=2)[CH2:34][CH2:33]1

Participants

3

Reactant 1

HCID 68328327HCID 68328327, compound

Product 1

HCID 68328329HCID 68328329, compoundYield 22.7%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of tert-butyl 5-(5-amino-1,3,4-thiadiazol-2-yl)-3-(6-morpholinopyridin-2-yl)-1H-indole-1-carboxylate (212 mg, 0.443 mmol) in DCM/TFA (1:1, 4 mL) was stirred at RT for 1 h, then the solvent was removed. The residue was diluted with DCM and washed with sat. NaHCO3. The organic layer was dried, filtered and concentrated. The residue was purified with silica gel chromatography (eluting with 0.5-4.5% MeOH in DCM) to give 5-(3-(6-morpholinopyridin-2-yl)-1H-indol-5-yl)-1,3,4-thiadiazol-2-amine (38.0 mg, 0.100 mmol, 22.7%) as a light brown solid. MS (ESI, pos. ion) m/z: 379 (M+1); 1H NMR (400 MHz, DMSO-d6) δ ppm 11.67 (1H, d, J=2.2 Hz), 8.82 (1H, d, J=1.6 Hz), 8.11 (1H, d, J=2.5 Hz), 7.74 (1H, dd, J=8.6, 1.8 Hz), 7.53-7.62 (1H, m), 7.48 (1H, d, J=8.6 Hz), 7.30 (1H, s), 7.22 (1H, d, J=7.4 Hz), 6.64 (1H, d, J=8.4 Hz), 3.79-3.93 (4H, m), 3.55-3.67 (4H, m).

Workup

  1. customthe solvent was removed
  2. additionThe residue was diluted with DCM
  3. washwashed with sat. NaHCO3
  4. customThe organic layer was dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified with silica gel chromatography (eluting with 0.5-4.5% MeOH in DCM)

Sources & evidence

ORD record
ord-8255cecd4256462fbd9b11697c4d54f4
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

Loading…