Ammonia → HCID 68328309, compound

HRID 634124Notes

Reaction equation

HRID 634124 reaction equation
CS([C:5]1[S:9][C:8]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15](C(OC(C)(C)C)=O)[CH:14]=[C:13]3[C:26]2[N:31]=[C:30]([N:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)[CH:29]=[CH:28][N:27]=2)=[N:7][N:6]=1)(=O)=O.[NH3:38].O>CS(C)=O>[O:35]1[CH2:34][CH2:33][N:32]([C:30]2[CH:29]=[CH:28][N:27]=[C:26]([C:13]3[C:12]4[C:16](=[CH:17][CH:18]=[C:10]([C:8]5[S:9][C:5]([NH2:38])=[N:6][N:7]=5)[CH:11]=4)[NH:15][CH:14]=3)[N:31]=2)[CH2:37][CH2:36]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 962WaterHCID 68328145HCID 68328145, compound

Product 1

HCID 68328309HCID 68328309, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

A sealed tube was charged with tert-butyl 5-(5-(methylsulfonyl)-1,3,4-thiadiazol-2-yl)-3-(4-morpholinopyrimidin-2-yl)-1H-indole-1-carboxylate (1.7 g, 3.3 mmol) in DMSO (17 mL) saturated with NH3. The reaction was heated at 110° C. for 7 h, then the mixture was poured into H2O. The mixture was extracted with EtOAc and the combined organic layers were dried, filtered and concentrated. The residue was purified with silica gel chromatography to give 5-(3-(4-morpholinopyrimidin-2-yl)-1H-indol-5-yl)-1,3,4-thiadiazol-2-amine (65 mg, 5%). MS (ESI, pos. ion) m/z: 380.1 (M+1). 1H-NMR (DMSO-d6, 300 MHz) δ: 11.89 (1H, s), 8.79 (1H, s), 8.28 (1H, d, J=6.3 Hz), 8.24 (1H, d, J=2.4 Hz), 7.75 (1H, dd, J=8.4, 1.5 Hz), 7.52 (1H, d, J=8.7 Hz), 7.32 (2H, s), 6.66 (1H, d, J=6.3 Hz), 3.81 (8H, brs).

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. customthe combined organic layers were dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified with silica gel chromatography

Sources & evidence

ORD record
ord-3ed716d419644a09a713ded0150a415f
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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