Water → HCID 57936190, compound

HRID 1434972Notes

Reaction equation

[CH3:1][C:2]1([CH3:27])[CH2:7][CH:6]([NH:8][C:9]2[N:14]=[C:13]([C:15]3[S:19][C:18]4[CH:20]=[C:21]([OH:24])[CH:22]=[CH:23][C:17]=4[CH:16]=3)[CH:12]=[CH:11][N:10]=2)[CH2:5][C:4]([CH3:26])([CH3:25])[NH:3]1.[H-].[Na+].[CH2:30](Br)[CH:31]=[CH2:32].O>CN(C)C=O>[CH2:32]([O:24][C:21]1[CH:22]=[CH:23][C:17]2[CH:16]=[C:15]([C:13]3[CH:12]=[CH:11][N:10]=[C:9]([NH:8][CH:6]4[CH2:7][C:2]([CH3:27])([CH3:1])[NH:3][C:4]([CH3:26])([CH3:25])[CH2:5]4)[N:14]=3)[S:19][C:18]=2[CH:20]=1)[CH:31]=[CH2:30]

Participants

Conditions

Temperature: 100 °C

Procedure

Compound of Example 153 (191 mg, 0.5 mmol) was suspended in 2 ml dimethylformamide. 24 mg (0.5 mmol) sodium hydride was added in small portions at room temperature. After 15 minutes 72 mg (0.6 mmol) allylbromide was added and the mixture was stirred at 100° C. for 2 hours. Then the cooled solution was poured on 200 ml water and extracted with EtOAc. The crude was purified by chromatography on silicagel (DCM/MeOH/ammonia:9/1/0.1). Yield: 110 mg (52%).

Workup

extractionextracted with EtOAc
customThe crude was purified by chromatography on silicagel (DCM/MeOH/ammonia:9/1/0.1)

Sources & evidence

ORD record: ord-9d21c0c2dfbd4801b99bd10a83c6c817
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07615562B2

Reaction notes

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