Hydrazine hydrate (1:1) → tert-butyl 4-(3-amino-1-(4-chlorophenyl)propylcarbamoyl)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidin-4-ylcarbamate

HRID 423057Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 423057
O.NN.[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([NH:25][C:26]([C:28]2([NH:43][C:44](=[O:50])[O:45][C:46]([CH3:49])([CH3:48])[CH3:47])[CH2:33][CH2:32][N:31]([C:34]3[C:35]4[CH:42]=[CH:41][NH:40][C:36]=4[N:37]=[CH:38][N:39]=3)[CH2:30][CH2:29]2)=[O:27])[CH2:12][CH2:13][N:14]2C(=O)C3C(=CC=CC=3)C2=O)=[CH:7][CH:6]=1>C(O)C>[NH2:14][CH2:13][CH2:12][CH:11]([NH:25][C:26]([C:28]1([NH:43][C:44](=[O:50])[O:45][C:46]([CH3:48])([CH3:47])[CH3:49])[CH2:29][CH2:30][N:31]([C:34]2[C:35]3[CH:42]=[CH:41][NH:40][C:36]=3[N:37]=[CH:38][N:39]=2)[CH2:32][CH2:33]1)=[O:27])[C:8]1[CH:7]=[CH:6][C:5]([Cl:4])=[CH:10][CH:9]=1

Komponenten

4

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 57750333tert-butyl 4-(1-(4-chlorophenyl)-3-(1,3-dioxoisoindolin-2-yl)propylcarbamoyl)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidin-4-ylcarbamate2×

Produkt 1

HCID 57750385tert-butyl 4-(3-amino-1-(4-chlorophenyl)propylcarbamoyl)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidin-4-ylcarbamateAusbeute 44,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Hydrazine monohydrate (10.32 μL) was added to a stirred suspension of tert-butyl 4-(1-(4-chlorophenyl)-3-(1,3-dioxoisoindolin-2-yl)propylcarbamoyl)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidin-4-ylcarbamate (Intermediate 37) (14 mg) in ethanol (1.0 mL) under argon. The resulting suspension was stirred at room temperature for 3 days. The mixture was filtered and was purified by preparative HPLC using a Waters X-Bridge reverse-phase column (C-18, 5 microns silica, 19 mm diameter, 100 mm length) and decreasingly polar mixtures of water (containing 0.2% ammonium carbonate) and acetonitrile as eluent. Pure fractions were evaporated to dryness to afford tert-butyl 4-(3-amino-1-(4-chlorophenyl)propylcarbamoyl)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidin-4-ylcarbamate as a white powder (5.00 mg, 44.5%).

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. customwas purified by preparative HPLC
  3. customPure fractions were evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-4bbb9905c5544e94b35984078b242d3a
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101623B2

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