Ammonia → HCID 68328565, compound

HRID 634131Notes

Reaction equation

HRID 634131 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[N:13]=[C:12]([C:14]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([C:23]5[S:24][C:25](S(C)(=O)=O)=[N:26][N:27]=5)[CH:21]=4)[N:16](C(OC(C)(C)C)=O)[CH:15]=3)[CH:11]=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[NH3:39].CCOC(C)=O>CS(C)=O>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[N:13]=[C:12]([C:14]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([C:23]5[S:24][C:25]([NH2:39])=[N:26][N:27]=5)[CH:21]=4)[NH:16][CH:15]=3)[CH:11]=[CH:10][CH:9]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 8857Ethyl AcetateHCID 68328781HCID 68328781, compound

Product 1

HCID 68328565HCID 68328565, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

A sealed tube was charged with tert-butyl 3-(6-(4-methylpiperazin-1-yl)pyridin-2-yl)-5-(5-(methylsulfonyl)-1,3,4-thiadiazol-2-yl)-1H-indole-1-carboxylate (300 mg, 0.541 mmol) followed by ammonia in DMSO (10 mL). The reaction was heated at 120° C. for 4 h. Ice/H2O and EtOAc were added to the mixture. The organic layer was separated and the aqueous layer was extracted with EtOAc. The combined organic layer was dried, filtered and concentrated. The residue was purified with RP-HPLC to give 5-(3-(6-(4-methylpiperazin-1-yl)pyridin-2-yl)-1H-indol-5-yl)-1,3,4-thiadiazol-2-amine (40 mg, 19%). MS (ESI, pos. ion) m/z: 392.1 (M+1); 1H-NMR (DMSO-d6, 300 MHz) δ 11.76 (1H, s), 10 (1H, brs), 8.8 (1H, s), 8.16 (1H, s), 7.5-7.67 (4H, m), 7.28-7.3 (1H, d), 6.75-6.79 (1H, d), 4.54-4.57 (2H, d), 3.6-3.65 (2H, d), 3.17-3.24 (4H, m), 2.91 (3H, s).

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with EtOAc
  3. customThe combined organic layer was dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified with RP-HPLC

Sources & evidence

ORD record
ord-3a22429923f04fa78830482686a664a4
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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