Phthalimide → HCID 66835990, compound

HRID 2404465Notes

Reaction equation

[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([O:24][CH:25]1[CH2:30][CH2:29][N:28]([CH3:31])[CH2:27][CH2:26]1)[C:11]1[CH:12]=[C:13]([S:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]O)[CH:14]=[CH:15][CH:16]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:51]1(=[O:61])[NH:55][C:54](=[O:56])[C:53]2=[CH:57][CH:58]=[CH:59][CH:60]=[C:52]12.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([O:24][CH:25]1[CH2:30][CH2:29][N:28]([CH3:31])[CH2:27][CH2:26]1)[C:11]1[CH:12]=[C:13]([S:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][N:55]2[C:51](=[O:61])[C:52]3[C:53](=[CH:57][CH:58]=[CH:59][CH:60]=3)[C:54]2=[O:56])[CH:14]=[CH:15][CH:16]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 5-{3-[(1H-benzimidazol-2-yl)(1-methylpiperidin-4-yloxy)methyl]phenylsulfanyl}pentan-1-ol (35 mg) in tetrahydrofuran are added triphenylphosphine (31 mg) and phthalimide (18 mg). The reaction mixture is cooled to 0° C. and diethyl azodicarboxylate (31 μL) is added. The reaction mixture is stirred at 0° C. for 30 minute. The mixture is evaporated to dryness and the residue is purified by chromatography (gradient dichloromethane/methanol/ammonia from 98/2/0.2 to 95/5/0.5) to give 2-(5-{3-[(1H-benzimidazol-2-yl)(1-methylpiperidin-4-yloxy)methyl]phenylsulfanyl}pentyl)isoindole-1,3-dione (example 305B).

Workup

customThe mixture is evaporated to dryness
customthe residue is purified by chromatography (gradient dichloromethane/methanol/ammonia from 98/2/0.2 to 95/5/0.5)

Sources & evidence

ORD record: ord-9cc4f2a9136046dabcc0ed44eade6d16
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802664B2

Reaction notes

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