5-(3-(6-(isopropylamino)pyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,2,4-thiadiazol-3-amine → 5-(3-(6-(isopropylamino)pyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-1,2,4-thiadiazol-3-amine

HRID 634258Notes

Reaction equation

HRID 634258 reaction equation
[CH:1]([NH:4][C:5]1[N:10]=[C:9]([C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20]4[S:24][N:23]=[C:22]([NH:25]CC5C=CC(OC)=CC=5)[N:21]=4)[CH:18]=3)[N:13]([S:35]([C:38]3[CH:44]=[CH:43][C:41]([CH3:42])=[CH:40][CH:39]=3)(=[O:37])=[O:36])[CH:12]=2)[CH:8]=[N:7][CH:6]=1)([CH3:3])[CH3:2]>C(O)(C(F)(F)F)=O>[CH:1]([NH:4][C:5]1[N:10]=[C:9]([C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20]4[S:24][N:23]=[C:22]([NH2:25])[N:21]=4)[CH:18]=3)[N:13]([S:35]([C:38]3[CH:39]=[CH:40][C:41]([CH3:42])=[CH:43][CH:44]=3)(=[O:36])=[O:37])[CH:12]=2)[CH:8]=[N:7][CH:6]=1)([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 683286605-(3-(6-(isopropylamino)pyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,2,4-thiadiazol-3-amine

Product 1

HCID 683288335-(3-(6-(isopropylamino)pyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-1,2,4-thiadiazol-3-amineYield 123.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 5-(3-(6-(isopropylamino)pyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,2,4-thiadiazol-3-amine (0.5 g, 0.80 mmol) in TFA (5 mL) was heated in Biotage microwave at 100° C. for 30 min. TFA was removed in vacuo and the residue was washed with Et2O (10 mL) to give the crude 5-(3-(6-(isopropylamino)pyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-1,2,4-thiadiazol-3-amine (0.5 g) as an off yellow solid, which was used for next step without any purification. MS (ESI, pos. ion) m/z: 506.0 (M+1).

Workup

  1. customTFA was removed in vacuo
  2. washthe residue was washed with Et2O (10 mL)

Sources & evidence

ORD record
ord-daeea5404a4a4ed687106804df8b30e0
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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