N-Iodosuccinimide → HCID 178468251, compound

HRID 2114567Notes

Reaction equation

[I:1]N1C(=O)CCC1=O.[F:9][C:10]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:11]=1[O:12][C:13]1[N:18]=[C:17]2[NH:19][N:20]=[CH:21][C:16]2=[C:15]([NH:22][CH2:23][C@H:24]([OH:26])[CH3:25])[N:14]=1>CN(C=O)C>[F:9][C:10]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:11]=1[O:12][C:13]1[N:18]=[C:17]2[NH:19][N:20]=[C:21]([I:1])[C:16]2=[C:15]([NH:22][CH2:23][CH:24]([OH:26])[CH3:25])[N:14]=1

Participants

Conditions

Temperature: 80 °C

Procedure

N-iodo succinimide (35 mg. 0.157 mmol) was dissolved in 3 mL of DMF, and (R)-1-[6-(2,4-Difluoro-phenoxy)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino]-propan-2-ol (42 mg, 0.131 mmol) was added. The reaction mixture was heated to 80° C. for two hours, after which an additional 35 mg of N-iodo succinimide was added. After heating for two more hours at 80° C., an additional 35 mg of N-iodo succinimide was added. The reaction mixture was heated at 80° C. for 5 more hours, then was cooled to room temperature. The reaction mixture was quenched by addition to water, and was partitioned between water and ethyl acetate. The organic layer was separated, dried over MgSO4, filtered, and evaporated under reduced pressure to give 64 mg of 1-[6-(2,4-Difluoro-phenoxy)-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino]-propan-2-ol. Mass Spec. M+H=448.

Workup

temperatureAfter heating for two more hours at 80° C.
temperatureThe reaction mixture was heated at 80° C. for 5 more hours
temperaturewas cooled to room temperature
customThe reaction mixture was quenched by addition to water
customwas partitioned between water and ethyl acetate
customThe organic layer was separated
dry with materialdried over MgSO4
filtrationfiltered
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-70bea1e428ec4654885bbf07f8e211ea
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07435731B2

Reaction notes

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