HCID 68328288, compound → HCID 68328581, compound

HRID 634096Notes

Reaction equation

HRID 634096 reaction equation
COC1C=CC(C[NH:8][C:9]2[O:10][C:11]([C:14]3[CH:15]=[C:16]4[C:20](=[CH:21][CH:22]=3)[N:19]([S:23]([C:26]3[CH:32]=[CH:31][C:29]([CH3:30])=[CH:28][CH:27]=3)(=[O:25])=[O:24])[CH:18]=[C:17]4[C:33]3[N:38]=[C:37]([N:39]4[CH2:44][CH2:43][CH2:42][CH2:41][CH:40]4[CH3:45])[CH:36]=[CH:35][N:34]=3)=[N:12][N:13]=2)=CC=1>C(O)(C(F)(F)F)=O>[CH3:45][CH:40]1[CH2:41][CH2:42][CH2:43][CH2:44][N:39]1[C:37]1[CH:36]=[CH:35][N:34]=[C:33]([C:17]2[C:16]3[C:20](=[CH:21][CH:22]=[C:14]([C:11]4[O:10][C:9]([NH2:8])=[N:13][N:12]=4)[CH:15]=3)[N:19]([S:23]([C:26]3[CH:27]=[CH:28][C:29]([CH3:30])=[CH:31][CH:32]=3)(=[O:25])=[O:24])[CH:18]=2)[N:38]=1

Participants

3

Reactant 1

HCID 68328288HCID 68328288, compound

Product 1

HCID 68328581HCID 68328581, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
120 °C

Procedure

N-(4-Methoxybenzyl)-5-(3-(4-(2-methylpiperidin-1-yl)pyrimidin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine (313 mg, 0.482 mmol) in a 20 mL glass microwave tube was dissolved in TFA (3.00 mL). The tube was sealed, and the solution was heated in an Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Uppsala, Sweden) at 120° C. for 20 min. The excess TFA was removed, the crude residue treated with 1N NaOH and extracted with EtOAc (2×50 mL). The combined organic layers were dried over MgSO4, filtered and concentrated to give the crude material: MS (ESI, pos ion) m/z 530.2 (M+1).

Workup

  1. customThe tube was sealed
  2. customThe excess TFA was removed
  3. additionthe crude residue treated with 1N NaOH
  4. extractionextracted with EtOAc (2×50 mL)
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ee7840e7a45548a893bc924f5d657126
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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