1-Hydroxybenzotriazole → HCID 68328865, compound

HRID 634316Notes

Reaction equation

HRID 634316 reaction equation
[CH:1]([NH:4][C:5]1[O:9][C:8]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15]([S:19]([C:22]2[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=2)(=[O:21])=[O:20])[CH:14]=[C:13]3[C:29]2[N:34]=[C:33]([C:35](O)=[O:36])[CH:32]=[CH:31][CH:30]=2)=[N:7][N:6]=1)([CH3:3])[CH3:2].C1C[N:41]([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)[CH2:40]C1.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.Cl.CN>CN(C=O)C>[CH:1]([NH:4][C:5]1[O:9][C:8]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15]([S:19]([C:22]2[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=2)(=[O:21])=[O:20])[CH:14]=[C:13]3[C:29]2[N:34]=[C:33]([C:35]([NH:41][CH3:40])=[O:36])[CH:32]=[CH:31][CH:30]=2)=[N:7][N:6]=1)([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 6364545Methylamine hydrochlorideHCID 68328685HCID 68328685, compound

Product 1

HCID 68328865HCID 68328865, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-(5-(5-(isopropylamino)-1,3,4-oxadiazol-2-yl)-1-tosyl-1H-indol-3-yl)picolinic acid (150 mg, 0.29 mmol) in DMF (3 mL) was added PyBOP (226 mg, 0.439 mmol), HOBt (59 mg, 0.435 mmol) and DIPEA (0.15 mL, 0.87 mmol). Methylamine hydrochloride (23 mg, 0.348 mmol) was added and the reaction was stirred for 2 h under Ar at RT. The reaction was quenched with water (200 mL) to get a brown precipitate. The precipitate was filtered, washed with water (2×100 mL) and dried. The crude product was purified with basic alumina chromatography (eluting with EtOAc) to give 6-(5-(5-(isopropylamino)-1,3,4-oxadiazol-2-yl)-1-tosyl-1H-indol-3-yl)-N-methylpicolinamide (150 mg, 98%). MS (ESI, pos. ion) m/z: 531.2 (M+1).

Workup

  1. customThe reaction was quenched with water (200 mL)
  2. customto get a brown precipitate
  3. filtrationThe precipitate was filtered
  4. washwashed with water (2×100 mL)
  5. customdried
  6. customThe crude product was purified with basic alumina chromatography (eluting with EtOAc)

Sources & evidence

ORD record
ord-b0949976c5d743c7aa07f2aa692a15ae
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

Loading…