Trifluoroacetic acid → AZD5363 (Capivasertib)

HRID 422991Notizen

Reaktionsgleichung

C(O)(C(F)(F)F)=O.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([NH:19][C:20]([C:22]2([NH:37]C(=O)OC(C)(C)C)[CH2:27][CH2:26][N:25]([C:28]3[C:29]4[CH:36]=[CH:35][NH:34][C:30]=4[N:31]=[CH:32][N:33]=3)[CH2:24][CH2:23]2)=[O:21])[CH2:16][CH2:17][OH:18])=[CH:11][CH:10]=1>ClCCl>[NH2:37][C:22]1([C:20]([NH:19][CH:15]([C:12]2[CH:11]=[CH:10][C:9]([Cl:8])=[CH:14][CH:13]=2)[CH2:16][CH2:17][OH:18])=[O:21])[CH2:23][CH2:24][N:25]([C:28]2[C:29]3[CH:36]=[CH:35][NH:34][C:30]=3[N:31]=[CH:32][N:33]=2)[CH2:26][CH2:27]1

Komponenten

Reaktionsbedingungen

Temperatur: 20 °C

Versuchsvorschrift

TFA (0.7 mL) was added to a suspension of tert-butyl 4-(1-(4-chlorophenyl)-3-hydroxypropylcarbamoyl)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidin-4-ylcarbamate (Intermediate 36) (175 mg, 0.33 mmol) in dichloromethane (7 mL) under argon. The resulting solution was stirred at 20° C. for 16 hours. The solvents were removed in vacuo and the reaction mixture was purified by preparative HPLC using a Waters X-Bridge reverse-phase column (C-18, 5 microns silica, 19 mm diameter, 100 mm length) with decreasingly polar mixtures of water (containing 0.2% ammonium carbonate) and acetonitrile as eluent. The pure fractions were evaporated to dryness to afford 4-amino-N-(1-(4-chlorophenyl)-3-hydroxypropyl)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide (99 mg, 69.8%) as a white powder.

Aufarbeitung

customThe solvents were removed in vacuo
customthe reaction mixture was purified by preparative HPLC
customThe pure fractions were evaporated to dryness

Quellen und Nachweise

ORD-Eintrag: ord-d6179294348b40819619eb13de7fddb0
Quelldatensatz: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08101623B2

Notizen zur Reaktion

Wird geladen…