Tetrabutylammonium Fluoride → HCID 178432254, compound

HRID 513827Notes

Reaction equation

[NH2:1][C:2]1[N:6]([C:7]2[CH:16]=[CH:15][C:10]3[NH:11][C:12]([CH3:14])=[N:13][C:9]=3[CH:8]=2)[N:5]=[CH:4][C:3]=1[C:17]([C:19]1[N:20](S(C2C=CC=CC=2)(=O)=O)[C:21]2[C:26]([CH:27]=1)=[CH:25][CH:24]=[C:23]([CH2:28][N:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1)[CH:22]=2)=[O:18].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[NH2:1][C:2]1[N:6]([C:7]2[CH:16]=[CH:15][C:10]3[NH:11][C:12]([CH3:14])=[N:13][C:9]=3[CH:8]=2)[N:5]=[CH:4][C:3]=1[C:17]([C:19]1[NH:20][C:21]2[C:26]([CH:27]=1)=[CH:25][CH:24]=[C:23]([CH2:28][N:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1)[CH:22]=2)=[O:18]

Participants

Conditions

Temperature: 65 °C

Procedure

[5-Amino-1-(2-methyl-1H-benzimidazol-5-yl)-1H-pyrazol-4-yl]-(1-benzenesulfonyl-6-morpholin-4-ylmethyl-1H-indol-2-yl)-methanone (132 mg, 0.22 mmol) was dissolved in tetrahydrofuran (THF) (1.0 ml), and then a tetrahydrofuran (THF) solution of 1 M tetrabutylammonium fluoride (0.46 ml, 0.46 mmol) was added thereto. The mixture was heated at 65° C. with stirring for 22 hours. The reaction mixture was then cooled to room temperature, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (dichloromethane/methanol=100/10) to give [5-amino-1-(2-methyl-1H-benzimidazol-5-yl)-1H-pyrazol-4-yl]-(6-morpholin-4-ylmethyl-1H-indol-2-yl)-methanone as a yellow solid (74 mg, 75%).

Workup

temperatureThe reaction mixture was then cooled to room temperature
concentrationconcentrated under reduced pressure
customThe resulting residue was purified by silica gel column chromatography (dichloromethane/methanol=100/10)

Sources & evidence

ORD record: ord-6c12b49acb8341f78c97c3f9ba04eaac
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102692B2

Reaction notes

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