Phosphorus oxychloride → HCID 68328277, compound

HRID 634328Notes

Reaction equation

HRID 634328 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]3[O:21][C:22]([NH:25][CH:26]([CH3:28])[CH3:27])=[N:23][N:24]=3)[CH:18]=2)[N:13]([S:29]([C:32]2[CH:38]=[CH:37][C:35]([CH3:36])=[CH:34][CH:33]=2)(=[O:31])=[O:30])[CH:12]=1.Cl.[CH3:40][NH2:41].O=P(Cl)(Cl)Cl>N1C=CC=CC=1>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:41][CH3:40])=[O:7])=[CH:4][C:3]=1[C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]3[O:21][C:22]([NH:25][CH:26]([CH3:27])[CH3:28])=[N:23][N:24]=3)[CH:18]=2)[N:13]([S:29]([C:32]2[CH:38]=[CH:37][C:35]([CH3:36])=[CH:34][CH:33]=2)(=[O:31])=[O:30])[CH:12]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 6364545Methylamine hydrochlorideHCID 68328183HCID 68328183, compound

Product 1

HCID 68328277HCID 68328277, compoundYield 48.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 4-fluoro-3-(5-(5-(isopropylamino)-1,3,4-oxadiazol-2-yl)-1-tosyl-1H-indol-3-yl)benzoic acid (500 mg, 0.936 mmol) and methylamine hydrochloride (97 mg, 1.40 mmol) in pyridine (10 mL) was added POCl3 (0.13 mL, 1.40 mmol). The reaction was stirred at RT for 1 h, then quenched with ice cold water (20 mL) to get a 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 4-fluoro-3-(5-(5-(isopropylamino)-1,3,4-oxadiazol-2-yl)-1-tosyl-1H-indol-3-yl)-N-methylbenzamide (250 mg, 48%). MS (ESI, pos. ion) m/z: 548.2 (M+1).

Workup

  1. customquenched with ice cold water (20 mL)
  2. customto get a 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-a25d513fd9764d22b044e1ae744da403
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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