Hydrochloric Acid → HCID 66628289, compound

HRID 1046841Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[N:14]3[N:15]=[C:16]([N:18]4C(=O)C5C(=CC=CC=5)C4=O)[N:17]=[C:13]3[N:12]([C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:38])([F:37])[F:36])[CH:30]=3)[C:11]([CH3:39])=[C:10]2[C:40]#[N:41])=[C:5]([S:42]([CH3:45])(=[O:44])=[O:43])[CH:4]=1)#[N:2].O.NN.Cl>C(O)C>[NH2:18][C:16]1[N:17]=[C:13]2[N:12]([C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:38])([F:36])[F:37])[CH:30]=3)[C:11]([CH3:39])=[C:10]([C:40]#[N:41])[CH:9]([C:6]3[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][C:5]=3[S:42]([CH3:45])(=[O:44])=[O:43])[N:14]2[N:15]=1

Participants

Conditions

Temperature: 85 °C

Procedure

In a pressure-proof glass tube, (rac)-7-[4-cyano-2-(methylsulfonyl)phenyl]-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-5-methyl-4-[3-(trifluoromethyl)phenyl]-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitrile (10 mg, 16 μmol) was initially charged in abs. ethanol (3 ml). Hydrazine hydrate (1.3 μl, 27 μmol, 1.7 eq.) was added, and the mixture was heated at 85° C. for 1 h. The reaction mixture was concentrated under reduced pressure, the residue was taken up in DMF (1 ml), 1 N hydrochloric acid (32 μl, 2 eq.) was added and the product was purified by preparative HPLC (Reprosil C18 column, 10 μm, 30×250 mm; mobile phase: acetonitrile-water-0.1% TFA). After lyophilization, the product was obtained as a solid (7.9 mg, quant.).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customthe product was purified by preparative HPLC (Reprosil C18 column, 10 μm, 30×250 mm; mobile phase: acetonitrile-water-0.1% TFA)
customAfter lyophilization, the product was obtained as a solid (7.9 mg, quant.)

Sources & evidence

ORD record: ord-6768e44bc65c46c5ac55ab2278dd9be5
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569314B2

Reaction notes

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