Reaktion #160898

Reaktionsgleichung

1-[4-(4-amino-6-ethylpyrrolo[2,1-f][1,2,4]triazin-5-yl)phenyl]-3-[4-(trifluoromethyl)pyridin-2-yl]urea

morpholine

formaldehyde

→

N-{4-[4-amino-6-ethyl-7-(morpholin-4-ylmethyl)pyrrolo[2,1-f][1,2,4]triazin-5-yl]phenyl}-N′-[4-(trifluoromethyl)pyridin-2-yl]urea

Lösungsmittel

acetic acid

acetic acid

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with NaHCO3
2. 2
   TrocknenThe organic layer was dried (MgSO4)
3. 3
   Einengenconcentrated
4. 4
   SonstigeThe pale orange solid was then triturated with ether
5. 5
   FiltrationThe desired product was collected by vacuum filtration (30 mg, 20%)
6. 6
   SonstigeLCMS RT=2.86

Vorschrift

A solution of 1-[4-(4-amino-6-ethylpyrrolo[2,1-f][1,2,4]triazin-5-yl)phenyl]-3-[4-(trifluoromethyl)pyridin-2-yl]urea (120 mg, 0.7 mmol) in acetic acid (2 mL) was treated with a mixture of morpholine (240 μL, 2.72 mmol) and formaldehyde (37%, 204 μL, 2.72 mmol) in acetic acid (1 mL). The reaction was heated to 60° C. overnight. The reaction was then diluted with EtOAc and washed with NaHCO3. The organic layer was dried (MgSO4) and concentrated. The pale orange solid was then triturated with ether. The desired product was collected by vacuum filtration (30 mg, 20%). 1H-NMR (DMSO-d6) δ 9.95 (bs, 1H), 9.82 (bs, 1H), 8.55 (d, J=4.1 Hz, 1H), 8.07 (s, 1H), 7.86 (s, 1H), 7.64 (d, J=6.8 Hz, 2H), 7.38-7.32 (m, 3H), 3.82 (s, 2H), 3.53-3.50 (m, 4H), 2.54-2.49 (m, 2H), 2.44-2.41 (m, 4H), 0.97 (t, J=7.5 Hz, 3H). MS [M+H]+=541.1; LCMS RT=2.86.

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