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Lithium Hydroxide → 3-Boc-amino-2-(4-chlorophenyl)-1-[4-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-piperazin-1-yl]-propan-1-one

HRID 1192411
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1192411
Cl.Cl.C1(S([N:12]2[C:16]3[N:17]=[CH:18][N:19]=[C:20]([N:21]4[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]4)[C:15]=3[C:14]([CH3:27])=[CH:13]2)(=O)=O)C=CC=CC=1.[C:28]([CH2:35][C:36]([NH2:47])([C:40]1[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][CH:41]=1)[C:37](O)=[O:38])([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Li+].[OH-].C([O-])(O)=O.[Na+]>CO>[C:28]([CH2:35][C:36]([NH2:47])([C:40]1[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][CH:41]=1)[C:37]([N:24]1[CH2:23][CH2:22][N:21]([C:20]2[C:15]3[C:14]([CH3:27])=[CH:13][NH:12][C:16]=3[N:17]=[CH:18][N:19]=2)[CH2:26][CH2:25]1)=[O:38])([O:30][C:31]([CH3:33])([CH3:34])[CH3:32])=[O:29]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 3939Lithium HydroxideHCID 516892Sodium BicarbonateHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 215841133-Boc-amino-2-(4-chlorophenyl)-propionic acidHCID 675377857-Benzenesulfonyl-5-methyl-4-piperazin-1-yl-7H-pyrrolo[2,3-d]pyrimidine dihydrochloride

Produkt 1

HCID 675403593-Boc-amino-2-(4-chlorophenyl)-1-[4-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-piperazin-1-yl]-propan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 7-benzenesulfonyl-5-methyl-4-piperazin-1-yl-7H-pyrrolo[2,3-d]pyrimidine dihydrochloride (35 mg. 0.081 mmol), 3-Boc-amino-2-(4-chlorophenyl)-propionic acid (27 mg, 0.089 mmol), and TEA (0.11 mL, 0.81 mmol) 1.2 mL DCM was added HBTU (34 mg, 0.089 mmol). The reaction mixture was stirred at room temperature 2 hours, after which 0.15 mL 3M LiOH and 1.0 mL MeOH were added. The reaction mixture was stirred at 35° C. for 3.5 hours, after which saturated NaHCO3 was added. The mixture was extracted with DCM, and the combined extracts were dried (Na2SO4), filtered, and concentrated. The crude was purified on silica gel (flushed with 1:1 DCM:EtOAc, then gradient to 1:4 DCM:EtOAc) to give 3-Boc-amino-2-(4-chlorophenyl)-1-[4-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-piperazin-1-yl]-propan-1-one, which was used in the next step.

Aufarbeitung

  1. stirringThe reaction mixture was stirred at 35° C. for 3.5 hours
  2. extractionThe mixture was extracted with DCM
  3. dry with materialthe combined extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude was purified on silica gel (
  7. customflushed with 1:1 DCM

Quellen und Nachweise

ORD-Eintrag
ord-ee9df9b45b1f42ea985fea10d8f2cf74
Quelldatensatz
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08680114B2

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