Isopropanol → HCID 86643032, compound

HRID 1879658Notes

Reaction equation

[N:1]1[CH:2]=[C:3]([C:10]2[C:14](=[O:15])[NH:13][C:12](=[O:16])[C:11]=2[C:17]2[C:23]3[CH:24]=[C:25]([F:38])[CH:26]=[C:27]4[CH2:28][CH:29]([C:30]([N:32]5[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]5)=[O:31])[N:21]([C:22]=34)[CH2:20][CH2:19][N:18]=2)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.[CH3:39][S:40]([OH:43])(=[O:42])=[O:41].C(O)(C)C>CO>[CH3:39][S:40]([OH:43])(=[O:42])=[O:41].[N:1]1[CH:2]=[C:3]([C:10]2[C:14](=[O:15])[NH:13][C:12](=[O:16])[C:11]=2[C:17]2[C:23]3[CH:24]=[C:25]([F:38])[CH:26]=[C:27]4[CH2:28][CH:29]([C:30]([N:32]5[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]5)=[O:31])[N:21]([C:22]=34)[CH2:20][CH2:19][N:18]=2)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

Conditions

Temperature: 64 °C

Procedure

Heat a slurry of 7-(2,5-dihydro-4-imidazo[1,2-a]pyridine-3-yl-2,5-dioxo-1H-pyrrol-3-yl)-9-fluoro-1,2,3,4-tetrahydro-2-(1-piperidinyl-carbonyl)-pyrrolo[3,2,1-jk][1,4]benzodiazepine (500 mg, 0.976 mmol) in methanol (2.5 mL) to 64° C. Add a solution of methanesulfonic acid (64 μL, 0.976 mmol) in methanol (1.0 mL) over 5 minutes. Stir the mixture at 64° C. for 15 minutes and then add isopropanol (5.0 mL) over 30 minutes. Allow the resulting slurry to cool to room temperature over 1 hour and then stir at room temperature for 4 hours. Filter the slurry, wash with isopropanol, and dry under reduced pressure at 42° C. to provide the title compound as an orange solid (478 mg, 88.5% (adjusted for 9.9% volatiles in starting material and 1.0% volatiles in product)).

Workup

temperatureAllow the resulting slurry to cool to room temperature over 1 hour
stirringstir at room temperature for 4 hours
filtrationFilter the slurry
washwash with isopropanol
customdry under reduced pressure at 42° C.

Sources & evidence

ORD record: ord-8739a5655d514c759fc52a749c32adf3
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318713B2

Reaction notes

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