Water → HCID 58980117, compound

HRID 28853

Reaction equation

HRID 28853 reaction equation
[CH2:1]([N:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[NH:14][CH:15]=[CH:16][C:9]=23)[C:5]([C:17]2[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=2)=[N:4]1)[CH3:2].N1C=CC=CC=1.[CH:30]([N:33]=[C:34]=[O:35])([CH3:32])[CH3:31].O>ClCCl>[CH2:1]([N:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[NH:14][CH:15]=[CH:16][C:9]=23)[C:5]([C:17]2[CH:23]=[CH:22][C:20]([NH:21][C:34]([NH:33][CH:30]([CH3:32])[CH3:31])=[O:35])=[CH:19][CH:18]=2)=[N:4]1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 61277Isopropyl isocyanateHCID 689998134-[1-ethyl-4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-3-yl]aniline

Product 1

HCID 58980117HCID 58980117, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-[1-ethyl-4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-3-yl]aniline (0.19 mmol) in dichloromethane (1 mL) was treated with pyridine (0.39 mmol) and isopropyl isocyanate (0.39 mmol). The reaction mixture was stirred for 18 h at room temperature and poured into water (1 mL), followed by extraction with (3×3 mL) ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated in vacuo. Purification of the residue by Gilson reverse phase HPLC provided the title product as a white powder (45%). ESMS [M+H]+: 389.2

Workup

  1. extractionfollowed by extraction with (3×3 mL) ethyl acetate
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customPurification of the residue by Gilson reverse phase HPLC

Sources & evidence

ORD record
ord-1beb9e6f6a7546959165bcc9db517abb
Source dataset
uspto-grants-2008_09
Patent number
US07419988B2

Linked notes

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