1-Hydroxybenzotriazole → HCID 18976139, compound

HRID 2393592Notes

Reaction equation

HRID 2393592 reaction equation
Cl.[NH2:2][CH:3]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[N:5]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[C:4]1=[O:21].[CH:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[C:24]([C:32]([O-])=[O:33])[N:23]=1.[Na+].ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O>[F:20][C:17]1[CH:18]=[CH:19][C:14]([N:5]2[C:6]3[C:11](=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[CH:7]=3)[CH:3]([NH:2][C:32]([C:24]3[N:23]=[CH:22][C:31]4[C:26]([CH:25]=3)=[CH:27][CH:28]=[CH:29][CH:30]=4)=[O:33])[C:4]2=[O:21])=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18976159HCID 18976159, compoundHCID 23722236HCID 23722236, compound

Product 1

HCID 18976139HCID 18976139, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension of 2.00 g of 3-amino-1-(4-fluorophenyl)-2,3-dihydro-6-methoxy-1H-indol-2-one hydrochloride, 1.33 g of sodium isoquinoline-3-carboxylate and 0.88 g of 1-hydroxybenzotriazole in 10 ml of anhydrous dimethylformamide was added 1.49 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride under ice cooling. The whole was stirred for 30 minutes. The reaction mixture was extracted by pouring a mixed solvent of ethyl acetate-tetrahydrofuran (2:1). The extract was washed with water, dried and evaporated. The residue was triturated with a mixed solvent of ethyl acetate and tetrahydrofuran to afford 2.60 g of N-[1(4-fluorophenyl)-2,3-dihydro-6-methoxy-2-oxo-1H-indol-3-yl]-3-isoquinolinecarboxamide as a powder. Melting point: 219° to 220° C.

Workup

  1. extractionThe reaction mixture was extracted
  2. additionby pouring a mixed solvent of ethyl acetate-tetrahydrofuran (2:1)
  3. washThe extract was washed with water
  4. customdried
  5. customevaporated
  6. customThe residue was triturated with a mixed solvent of ethyl acetate and tetrahydrofuran

Sources & evidence

ORD record
ord-bbf19579dce84eab89bf0a7864482bd6
Source dataset
uspto-grants-1998_09
Patent number
US05807883

Reaction notes

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