1,3-Propanediamine → HCID 86710012, compound

HRID 1855306Notes

Reaction equation

[CH2:1]([NH2:5])[CH2:2][CH2:3][NH2:4].[Br:6][C:7]1[CH:20]=[C:19]2[C:10]([O:11][C:12]3[C:13]([F:29])=[CH:14][C:15]([O:27][CH3:28])=[CH:16][C:17]=3[C:18]32[C:24](=S)[S:23][C:22](=S)[NH:21]3)=[CH:9][CH:8]=1>CCO>[Br:6][C:7]1[CH:20]=[C:19]2[C:10]([O:11][C:12]3[C:13]([F:29])=[CH:14][C:15]([O:27][CH3:28])=[CH:16][C:17]=3[C:18]32[C:24]2=[N:5][CH2:1][CH2:2][CH2:3][N:4]2[C:22](=[S:23])[NH:21]3)=[CH:9][CH:8]=1

Participants

Conditions

Temperature: 65 °C

Procedure

Propane-1,3-diamine (4.12 mL, 47.8 mmol) and 7′-bromo-4′-fluoro-2′-methoxyspiro[thiazolidine-4,9′-xanthene]-2,5-dithione (4.23 g, 9.56 mmol) were combined in 50 ml of EtOH and heated to 65° C. for 30 minutes. The solution was then concentrated. The product was purified via silica gel column chromatography (RediSep 330 g column) using 0-50% EtOAc in hexane to afford 7′-bromo-4′-fluoro-2′-methoxy-3,4-dihydro-2H-spiro[imidazo[1,5-a]pyrimidine-8,9′-xanthene]-6(7H)-thione (1.0 g, 2.231 mmol) as an off white solid. MS m/z=448.0 [M+H].

Workup

concentrationThe solution was then concentrated
customThe product was purified via silica gel column chromatography (RediSep 330 g column)

Sources & evidence

ORD record: ord-6366dbe93aed4dc7922dbb0ca81ca39e
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962859B2

Reaction notes

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