1-Pyrrolidinesulfonyl chloride → tert-Butyl 6-(3-fluoro-5-(pyrrolidine-1-sulfonamido)phenyl)pyrido[3,2-d]pyrimidin-4-ylcarbamate

HRID 1049919

Reaktionsgleichung

Reaktionsgleichung von HRID 1049919
[N:1]1([S:6](Cl)(=[O:8])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:10][C:11]1[CH:12]=[C:13]([C:18]2[CH:19]=[CH:20][C:21]3[N:22]=[CH:23][N:24]=[C:25]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[C:26]=3[N:27]=2)[CH:14]=[C:15]([F:17])[CH:16]=1>N1C=CC=CC=1>[F:17][C:15]1[CH:14]=[C:13]([C:18]2[CH:19]=[CH:20][C:21]3[N:22]=[CH:23][N:24]=[C:25]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:33])([CH3:32])[CH3:34])[C:26]=3[N:27]=2)[CH:12]=[C:11]([NH:10][S:6]([N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)(=[O:8])=[O:7])[CH:16]=1

Komponenten

4

Edukt 2

HCID 64839021-Pyrrolidinesulfonyl chlorideHCID 90032608Tert-butyl 6-(3-amino-5-fluorophenyl)pyrido[3,2-d]pyrimidin-4-ylcarbamate

Produkt 1

HCID 90054687tert-Butyl 6-(3-fluoro-5-(pyrrolidine-1-sulfonamido)phenyl)pyrido[3,2-d]pyrimidin-4-ylcarbamateAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Pyrrolidine-1-sulfonyl chloride (CAS 1689-02-7) (56 mg, 0.92 mmol) was added to a solution of tert-butyl 6-(3-amino-5-fluorophenyl)pyrido[3,2-d]pyrimidin-4-ylcarbamate (33-A) (300 mg, 0.84 mmol) in pyridine at ice bath. After the reaction mixture was stirred at 60° C. for 4 h, it was partitioned between water and EtOAc and purified by prep-TLC (PE:EtOAc=2:1) to give title product (250 mg, 61%).

Aufarbeitung

  1. customit was partitioned between water and EtOAc
  2. custompurified by prep-TLC (PE:EtOAc=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-2304f16ca18648a791a3763cbd5ea650
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09382241B2

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