Sodium Azide → HCID 178494231, compound

HRID 2110761Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

Sodium azide (10 mg, 0.15 mmol) is added to a stirred solution of (3-{6-[2-(2,4-dichloro-phenyl)-ethylamino]-2-methoxy-pyrimidin-4-yl}-phenyl)-difluoro-acetonitrile (50 mg, 0.11 mmol) in N,N′-dimethylformamide (4 mL) and the reaction is stirred for 4 hours at 80° C. The reaction is quenched with water, acidified to pH 2 (0.05 N HCl), extracted twice with ethyl acetate. The combined extracts is dried over sodium sulfate, filtered and concentrated in vacuo. The residue is diluted in toluene and concentrated in vacuo to afford [2-(2,4-dichloro-phenyl)-ethyl]-(6-{3-[difluoro-(1H-tetrazol-5-yl)-methyl]-phenyl}-2-methoxy-pyrimidin-4-yl)-amine [45 mg, Example 82(c)]. LCMS: RT=2.29 minutes, LCMS: 492, 494 (M+H). IC50=0.1 nM

Workup

customThe reaction is quenched with water
extractionextracted twice with ethyl acetate
dry with materialThe combined extracts is dried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
additionThe residue is diluted in toluene
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-d8d8dccd52714f2495a83aae95660709
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07517889B2

Reaction notes

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