Isopropylamine → 5-(3-iodo-1-tosyl-1H-indol-5-yl)-N-isopropyl-1,3,4-oxadiazol-2-amine

HRID 634209Notes

Reaction equation

HRID 634209 reaction equation
F[P-](F)(F)(F)(F)F.[N:8]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:12]2[CH:13]=CC=C[C:11]=2N=N1.[I:28][C:29]1[C:37]2[C:32](=[CH:33][CH:34]=[C:35]([C:38]3[O:42][C:41](=O)[NH:40][N:39]=3)[CH:36]=2)[N:31]([S:44]([C:47]2[CH:53]=[CH:52][C:50]([CH3:51])=[CH:49][CH:48]=2)(=[O:46])=[O:45])[CH:30]=1.CC(N)C.C(N(C(C)C)CC)(C)C>CN(C=O)C.O>[I:28][C:29]1[C:37]2[C:32](=[CH:33][CH:34]=[C:35]([C:38]3[O:42][C:41]([NH:8][CH:12]([CH3:13])[CH3:11])=[N:40][N:39]=3)[CH:36]=2)[N:31]([S:44]([C:47]2[CH:48]=[CH:49][C:50]([CH3:51])=[CH:52][CH:53]=2)(=[O:45])=[O:46])[CH:30]=1

Participants

7

Reactant 4

HCID 6363IsopropylamineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 683283805-(3-iodo-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2(3H)-one

Product 1

HCID 683289275-(3-iodo-1-tosyl-1H-indol-5-yl)-N-isopropyl-1,3,4-oxadiazol-2-amineYield 73.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

BOP (253 mg, 0.571 mmol) was added to a stirred mixture of 5-(3-iodo-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2(3H)-one (250 mg, 0.519 mmol), propan-2-amine (0.13 mL, 1.56 mmol) and diisopropylethylamine (0.18 mL, 1.04 mmol) in DMF (1.5 mL). The reaction was stirred at RT for 14 h then diluted with water and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4 and concentrated. Purification on the ISCO (12 g column, 20-70% EtOAc in Hex) afforded 5-(3-iodo-1-tosyl-1H-indol-5-yl)-N-isopropyl-1,3,4-oxadiazol-2-amine (199 mg, 73%) as a white amorphous solid. MS (ESI, pos. ion) m/z: 523.0 (M+1). 1H NMR (400 MHz, CDCl3) δ ppm 8.02 (1H, d, J=8.6 Hz), 7.95 (1H, d, J=8.4 Hz), 7.86 (1H, s), 7.76-7.82 (2H, m), 7.71-7.76 (1H, m), 7.28 (2H, s), 4.54 (1H, d, J=7.6 Hz), 3.94-4.05 (1H, m), 2.37 (3H, s), 1.34 (6H, d, J=6.5 Hz).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customPurification on the ISCO (12 g column, 20-70% EtOAc in Hex)

Sources & evidence

ORD record
ord-d0df176017b14c41bb5b0956a94a6a0d
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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