Cesium fluoride → 5-(1-Benzyl-hexahydro-pyrrolo[3,4-b]pyrrol-5-yl)-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine

HRID 1172573Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([NH2:8])[N:5]2[N:9]=[C:10]([C:12]3[O:13][CH:14]=[CH:15][CH:16]=3)[N:11]=[C:4]2[N:3]=1.[F-].[Cs+].[CH2:19]([N:26]1[CH2:33][CH2:32][CH:31]2[CH:27]1[CH2:28][NH:29][CH2:30]2)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CS(C)=O>[CH2:19]([N:26]1[CH2:33][CH2:32][CH:31]2[CH2:30][N:29]([C:2]3[CH:7]=[C:6]([NH2:8])[N:5]4[N:9]=[C:10]([C:12]5[O:13][CH:14]=[CH:15][CH:16]=5)[N:11]=[C:4]4[N:3]=3)[CH2:28][CH:27]12)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 120 °C

Procedure

5-Chloro-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine (0.5 mmol; see WO 99/43678 A1) was dissolved in 4 mL of DMSO along with 2-benzyl-2,7-diazabicyclo[3.3.0]octane (2 mmol; see U.S. Pat. No. 5,071,999) and 0.7 mmol of CsF. The reaction mixture was stirred at 120° C. for 8 hours. It was then cooled to room temperature and purified by preparative HPLC to afford the title compound. 1H NMR (400 Hz, DMSO-d6) 7.60 (d, J=1.0 Hz, 1H), 7.28 (br s, 2H), 7.22 (d, J=3.6 Hz, 1H), 7.0-7.2 (m, 5H), 6.68 (dd, J=3.6 Hz, 1.0 Hz, 1H) 5.2 (s, 1H), 3.8 (br s, 2H), 2.2-3.2 (m, 10H). m/z: 402 [M+H]+.

Workup

temperatureIt was then cooled to room temperature
custompurified by preparative HPLC

Sources & evidence

ORD record: ord-e56bbac8491341d0a1902adc7224eb27
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07834014B2

Reaction notes

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