1-Hydroxybenzotriazole → HCID 68328437, compound

HRID 634319Notes

Reaction equation

HRID 634319 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[CH:30]=[N:31][CH:32]=[C:33]([CH:37]=2)[C:34](O)=[O:35])=[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:23]=[CH:24][C:25]([CH3:26])=[CH:27][CH:28]=2)(=[O:21])=[O:20])[CH:14]=[C:13]3[C:29]2[CH:30]=[N:31][CH:32]=[C:33]([CH:37]=2)[C:34]([NH:41][CH3:40])=[O:35])=[N:7][N:6]=1)([CH3:2])[CH3:3]

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 6364545Methylamine hydrochlorideHCID 68328124HCID 68328124, compound

Product 1

HCID 68328437HCID 68328437, compoundYield 29.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(5-(5-(isopropylamino)-1,3,4-oxadiazol-2-yl)-1-tosyl-1H-indol-3-yl)nicotinic acid (500 mg, 0.967 mmol) in DMF (10 mL) was added PyBOP (755 mg, 1.45 mmol), HOBt (196 mg, 1.45 mmol) and DIPEA (0.50 mL, 2.9 mmol). Methylamine hydrochloride (77.7 mg, 1.160 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 5-(5-(5-(isopropylamino)-1,3,4-oxadiazol-2-yl)-1-tosyl-1H-indol-3-yl)-N-methylnicotinamide (150 mg, 29%). 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-fc8a363b407a40598bdba52e066f1691
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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