Isopropylamine → 5-chloro-6-{[5-chloro-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-1H-indazole-7-carboxylic acid isopropylamide

HRID 245629Notes

Reaction equation

HRID 245629 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[CH:28]=[N:27][NH:26][C:5]2=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[N:13]([C:18]3[C:23]([Cl:24])=[CH:22][CH:21]=[CH:20][N:19]=3)[N:14]=[C:15]([Cl:17])[CH:16]=1)[O:8][C:7]2=[O:25].[CH:29]([NH2:32])([CH3:31])[CH3:30]>O1CCCC1>[CH:29]([NH:32][C:7]([C:6]1[C:11]([NH:10][C:9]([C:12]2[N:13]([C:18]3[C:23]([Cl:24])=[CH:22][CH:21]=[CH:20][N:19]=3)[N:14]=[C:15]([Cl:17])[CH:16]=2)=[O:8])=[C:2]([Cl:1])[CH:3]=[C:4]2[C:5]=1[NH:26][N:27]=[CH:28]2)=[O:25])([CH3:31])[CH3:30]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 57990091HCID 57990091, compound

Product 1

HCID 579901125-chloro-6-{[5-chloro-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-1H-indazole-7-carboxylic acid isopropylamideYield 56.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 210 mg (0.40 mmol) of the above 5-chloro-7-[5-chloro-2-(3-chloro-pyridin-2-yl)-2H-pyrazol-3-yl]-1H-8-oxa-1,2,6-triaza-cyclopenta[a]naphthalen-9-one in 4.2 mL of tetrahydrofuran is added 110 μl (1.3 mmol) of isopropylamine. The reaction mixture is stirred for 4 hours at ambient temperature and then concentrated in vacuo. The residue is Purification of the residue by reverse-phase chromatography affords 111 mg (52%) of the product as a white solid; LC/MS:514/516 (M+Na)+.

Workup

  1. concentrationconcentrated in vacuo
  2. customPurification of the residue by reverse-phase chromatography

Sources & evidence

ORD record
ord-4ed1636b03e845e18a554ea4cd782512
Source dataset
uspto-grants-2014_02
Patent number
US08658801B2

Reaction notes

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