Prolinol → HCID 68313050, compound

HRID 1530530Notes

Reaction equation

Cl[C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][N:15]=1)[C:12]1[N:8]([CH:9]=[C:10]([C:16]3[N:20]([CH:21]([CH3:23])[CH3:22])[N:19]=[CH:18][N:17]=3)[N:11]=1)[CH2:7][CH2:6][O:5]2.[NH:24]1[CH2:28][CH2:27][CH2:26][CH:25]1[CH2:29][OH:30]>O>[CH3:22][CH:21]([N:20]1[C:16]([C:10]2[N:11]=[C:12]3[N:8]([CH:9]=2)[CH2:7][CH2:6][O:5][C:4]2[C:13]3=[CH:14][N:15]=[C:2]([N:24]3[CH2:28][CH2:27][CH2:26][CH:25]3[CH2:29][OH:30])[CH:3]=2)=[N:17][CH:18]=[N:19]1)[CH3:23]

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of 12-chloro-4-[1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6,13-triazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaene from Example 135 (500 mg, 1.51 mmol) and pyrrolidin-2-yl-methanol (1.00 g, 9.89 mmol) was stirred at 160° C. for 4 hr. The resulting mixture was poured into water and extracted with ethyl acetate, washed with brine, dried over MgSO4, filtered, and evaporated to give the crude product, which was purified by reverse phase combiflash eluting with 0-50% gradient of CH3CN in 0.5% NH4HCO3 to give (1-{4-[1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6,13-triazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaen-12-yl}pyrrolidin-2-yl)methanol as white solid (345 mg, 58% yield). LCMS (ESI) m/z: 396.2 [M+H+].

Workup

extractionextracted with ethyl acetate
washwashed with brine
dry with materialdried over MgSO4
filtrationfiltered
customevaporated
customto give the crude product, which
customwas purified by reverse phase combiflash
washeluting with 0-50% gradient of CH3CN in 0.5% NH4HCO3

Sources & evidence

ORD record: ord-8b642d8a3eba4376bb2fe2aa5b4596b7
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090628B2

Reaction notes

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