Water → HCID 178467902, compound

HRID 1181597Notes

Reaction equation

[OH:1][C@H:2]([CH2:21][NH:22][C:23]([CH3:36])([CH3:35])[CH2:24][C:25]1[CH:34]=[CH:33][C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=1)[CH2:3][O:4][CH:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[CH:15][CH:14]=1)[CH3:6].[Cl-].[NH4+].[N-:39]=[N+:40]=[N-:41].[Na+].O>CN(C)C=O>[CH3:36][C:23]([NH:22][CH2:21][C@@H:2]([OH:1])[CH2:3][O:4][CH:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[CH:14]=[CH:15][C:16]([C:19]2[NH:41][N:40]=[N:39][N:20]=2)=[CH:17][CH:18]=1)[CH3:6])([CH3:35])[CH2:24][C:25]1[CH:34]=[CH:33][C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=1

Participants

Conditions

Temperature: 115 °C

Procedure

2′-[1-[(2R)-2-Hydroxy-3-[[2-methyl-1-(naphthalen-2-yl)propan-2-yl]amino]propoxy]ethyl]biphenyl-4-carbonitrile (500 mg) obtained in Step 2 was dissolved in N,N-dimethylformamide (6.0 ml), ammonium chloride (535 mg) and sodium azide (676 mg) were successively added and the mixture was stirred overnight at 115° C. Water was added to the reaction mixture, and the precipitated solid was collected by filtration. The solid was dissolved in methanol, water was added and the mixture was concentrated under reduced pressure. The precipitated solid was collected by filtration to give the title compound (280 mg).

Workup

filtrationthe precipitated solid was collected by filtration
dissolutionThe solid was dissolved in methanol
additionwater was added
concentrationthe mixture was concentrated under reduced pressure
filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record: ord-b392f57696924a7a9761c7094cad5720
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07285572B2

Reaction notes

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