Trifluoroacetic acid → 5-(2-Benzyl-2H-indazol-6-yl)-7-pyrrolidin-3-ylmethyl-pyrrolo[2,1-f][1,2,4]triazin-4-ylamine

HRID 1972891Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1972891
C(OC([N:8]1[CH2:12][CH2:11][CH:10]([CH2:13][C:14]2[N:22]3[C:17]([C:18]([NH2:23])=[N:19][CH:20]=[N:21]3)=[C:16]([C:24]3[CH:25]=[CH:26][C:27]4[C:31]([CH:32]=3)=[N:30][N:29]([CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH:28]=4)[CH:15]=2)[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[CH2:33]([N:29]1[CH:28]=[C:27]2[C:31]([CH:32]=[C:24]([C:16]3[CH:15]=[C:14]([CH2:13][CH:10]4[CH2:11][CH2:12][NH:8][CH2:9]4)[N:22]4[C:17]=3[C:18]([NH2:23])=[N:19][CH:20]=[N:21]4)[CH:25]=[CH:26]2)=[N:30]1)[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 585297003-[4-Amino-5-(2-benzyl-2H-indazol-6-yl)-pyrrolo[2,1-f][1,2,4]triazin-7-ylmethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 585294185-(2-Benzyl-2H-indazol-6-yl)-7-pyrrolidin-3-ylmethyl-pyrrolo[2,1-f][1,2,4]triazin-4-ylamineAusbeute 31,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The product from Step 4 (0.10 g, 0.19 mmol) was dissolved in dichloromethane (3 mL) and TFA (0.14 mL, 1.95 mmol) was added. The mixture was stirred for 18 hours and concentrated. The residue was purified by preparative HPLC using 10-90% gradient of acetonitrile/water to provide 25 mg (31%) of the title compound. 1H-NMR (CD3OD-d4) 8.30-8.35 (m, 1H), 7.85-7.80 (m, 2 H), 7.67-7.64 (m, 1H), 7.40-7.22 (m, 5 H), 7.24 (dd, 1 H), 6.64 (s, 1 H), 5.67 (s, 2 H), 3.17-2.94 (m, 3 H), 2.77-2.68 (m, 2 H), 2.08-1.98 (m, 1 H), 1.70-1.59 (m, 1 H); LC-MS [M+H]+=424.2, RT=2.03 min.

Aufarbeitung

  1. concentrationconcentrated
  2. customThe residue was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-a5805f77a21e4b8abb3470cda92ed8b8
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08431695B2

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