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

HRID 1172571Notes

Reaction equation

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

Participants

Conditions

Temperature: 120 °C

Procedure

2-Benzyl-2,7-diazabicyclo[3.3.0]octane (1.2 mmol; see U.S. Pat. No. 5,071,999) was dissolved in 2 mL of DMSO along with 7-chloro-2-furan-2-yl-[1,2,4]triazolo[1,5-c]pyrimidin-5-ylamine (0.25 mmol; see U.S. Pat. No. 6,222,035 B1) and CsF (0.3 mmol). The reaction mixture was stirred at 120° C. for 18 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) 5.4 (s, 1H), 3.8 (br s, 2H), 2.2-3.2 (m, 10H). MS: m/z: 402 [M+H]+.

Workup

temperatureIt was then cooled to room temperature
custompurified by preparative HPLC

Sources & evidence

ORD record: ord-b7cee4d2ff364ad992880166d74ff656
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07834014B2

Reaction notes

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