Water → tert-Butyl (1S,2R)-2-(7-chloro-4-(1-methyl-1H-pyrazol-4-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)cyclohexylcarbamate

HRID 516001Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 516001
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[C:12]3[C:13](=[O:16])[NH:14][CH2:15][C:11]=3[CH:10]=[C:9]([NH:17][C@@H:18]3[CH2:23][CH2:22][CH2:21][CH2:20][C@@H:19]3[NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[N:8]=2)[CH:4]=[N:3]1.[Cl:32]N1C(=O)CCC1=O.O.C(Cl)(Cl)Cl>C(Cl)Cl>[Cl:32][C:10]1[C:11]2[CH2:15][NH:14][C:13](=[O:16])[C:12]=2[C:7]([C:5]2[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=2)=[N:8][C:9]=1[NH:17][C@@H:18]1[CH2:23][CH2:22][CH2:21][CH2:20][C@@H:19]1[NH:24][C:25](=[O:31])[O:26][C:27]([CH3:28])([CH3:30])[CH3:29]

Komponenten

6

Edukt 4

HCID 962WaterHCID 6212ChloroformHCID 31398Chlorosuccinimide2×HCID 86654709tert-Butyl (1S,2R)-2-(4-(1-methyl-1H-pyrazol-4-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)cyclohexylcarbamate

Produkt 1

HCID 86654711tert-Butyl (1S,2R)-2-(7-chloro-4-(1-methyl-1H-pyrazol-4-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)cyclohexylcarbamateAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of tert-butyl (1S,2R)-2-(4-(1-methyl-1H-pyrazol-4-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)cyclohexylcarbamate (30 mg, 0.070 mmol) and N-chlorosuccinimide (9.86 mg, 0.074 mmol) in DCM (1 mL) was stirred at RT overnight. Additional N-chlorosuccinimide (1 eq) was added and the mixture was stirred at RT for 3 h. Water and CHCl3 were added to the mixture and the organic phase was washed with brine, dried over MgSO4, and evaporated. The residue was purified by preparative HPLC to give the title compound (20 mg, 61.7%). 1H NMR (500 MHz, CDCl3) δ ppm 1.18-2.09 (m, 17 H), 4.02 (s, 3 H), 4.28-4.45 (m, 2 H), 5.80 (br s, 1 H), 8.39 (br s, 1 H), 9.03 (br s, 1 H). [M+H] calc'd for C22H29ClN6O3, 461; found, 461.

Aufarbeitung

  1. washthe organic phase was washed with brine
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. customThe residue was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-9a5f6e9830f042b489444236f1ff98ba
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09108970B2

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