1-Hydroxybenzotriazole → 4-[2-(Biphenyl-4-ylcarbamoyl)-acetyl]-piperazine-1-carboxylic acid tert-butyl ester

HRID 1665595Notizen

Reaktionsgleichung

C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[C:20]1([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:32])[CH2:28][C:29]([OH:31])=O)=[CH:22][CH:21]=1.CCN=C=NCCCN(C)C.Cl.[C:51]([O:55][C:56]([N:58]1[CH2:63][CH2:62][NH:61][CH2:60][CH2:59]1)=[O:57])([CH3:54])([CH3:53])[CH3:52]>CN(C=O)C.O>[C:51]([O:55][C:56]([N:58]1[CH2:63][CH2:62][N:61]([C:29](=[O:31])[CH2:28][C:27](=[O:32])[NH:26][C:23]2[CH:22]=[CH:21][C:20]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[CH:25][CH:24]=2)[CH2:60][CH2:59]1)=[O:57])([CH3:54])([CH3:52])[CH3:53]

Komponenten

Reaktionsbedingungen

Temperatur: 10 °C

Versuchsvorschrift

HOBt (570 mg, 4.2 mmol) and DIPEA (541 mg, 4.2 mmol) were added to a stirred solution of N-biphenyl-4-yl-malonamic acid (1 g, 3.5 mmol) in DMF (10 mL). The reaction mixture was cooled to 10° C. and EDCI.HCl (810 mg, 4.2 mmol) followed by piperazine-1-carboxylic acid tert-butyl ester (720 mg, 3.86 mmol) were added. The resulting reaction mixture was stirred at room temperature overnight. Water was then added and the resulting precipitate was filtered and dried to afford 1.4 g (93%) of 4-[2-(biphenyl-4-ylcarbamoyl)-acetyl]-piperazine-1-carboxylic acid tert-butyl ester. 1H NMR: (CDCl3): δ 8.6 (s, 1H), 7.9 (m, 2H), 7.7 (m, 2H), 7.65 (m, 1H), 7.5 (m, 3H), 7.4 (s, 1H), 4.1 (m, 2H), 3.6 (m, 4H), 3.4 (m, 2H), 3.1 (m, 2H).

Aufarbeitung

additionwere added
customThe resulting reaction mixture
filtrationthe resulting precipitate was filtered
customdried

Quellen und Nachweise

ORD-Eintrag: ord-3061fce965ca4b658210f52ccfc56fb6
Quelldatensatz: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08039463B2

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