Isopropylamine → HCID 68327956, compound

HRID 634242Notes

Reaction equation

HRID 634242 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[O:14][C:13](=O)[NH:12][N:11]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[CH:16]([NH2:19])([CH3:18])[CH3:17].C1(OC2C=CC=CC=2)C=CC=CC=1.CCN(C(C)C)C(C)C.CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.O>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[O:14][C:13]([NH:19][CH:16]([CH3:18])[CH3:17])=[N:12][N:11]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

8

Reactant 5

HCID 6363IsopropylamineHCID 7583Diphenyl EtherHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 68328544HCID 68328544, compound

Product 1

HCID 68327956HCID 68327956, compoundYield 62.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(1H-indol-5-yl)-1,3,4-oxadiazol-2(3H)-one (200 mg, 0.995 mmol) in DMF (2 mL) was added isopropyl amine (0.169 mL, 1.99 mmol), diphenyl ether (161 mg, 0.995 mmol), and DIPEA (0.34 mL, 1.99 mmol) and the reaction was stirred at RT for 5 min. To the above mixture at RT was added BOP reagent (461 mg, 1.045 mmol) and the reaction was further stirred for 18 h at RT. The mixture was treated with H2O (10 mL) to get off white precipitate. The precipitate was filtered, washed with H2O (10 mL) and dried. The solid was further triturated with petroleum ether (2×5 mL) to afford 5-(1H-indol-5-yl)-N-isopropyl-1,3,4-oxadiazol-2-amine (150 mg, 62%) as an off white solid. MS (ESI, pos. ion) m/z: 243.1 (M+1); 1H NMR (400 MHz, DMSO-d6): δ 11.40 (brs, 1H), 7.98 (s, 1H), 7.59 (dd, J=6.8, 1.6 Hz, 1H), 7.51 (t, J=7.2 Hz, 2H), 7.44 (m, 1H), 3.70-3.75 (m, 1H), 1.22 (d, J=6.4 Hz, 6H).

Workup

  1. stirringthe reaction was further stirred for 18 h at RT
  2. customto get off white precipitate
  3. filtrationThe precipitate was filtered
  4. washwashed with H2O (10 mL)
  5. customdried
  6. customThe solid was further triturated with petroleum ether (2×5 mL)

Sources & evidence

ORD record
ord-c1dc8271cb7c4244a94444678748277d
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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