Hydrochloric Acid → HCID 58032656, compound

HRID 1046897Notes

Reaction equation

[OH-].[Li+].[C:3]([C:5]1[CH:10]=[CH:9][C:8]([C@H:11]2[N:16]3[N:17]=[N:18][N:19]=[C:15]3[N:14]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=3)[C:13]([CH3:30])=[C:12]2[C:31]([O:33]CC)=[O:32])=[CH:7][CH:6]=1)#[N:4].Cl>C(O)C.C1COCC1.O>[C:3]([C:5]1[CH:6]=[CH:7][C:8]([C@H:11]2[N:16]3[N:17]=[N:18][N:19]=[C:15]3[N:14]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:28])([F:27])[F:29])[CH:21]=3)[C:13]([CH3:30])=[C:12]2[C:31]([OH:33])=[O:32])=[CH:9][CH:10]=1)#[N:4]

Participants

Conditions

Temperature: 55 °C

Procedure

The reaction was carried out under argon. Solid lithium hydroxide (15.8 mg, 660 μmol, 3 eq.) was added to a solution of ethyl (7R)-7-(4-cyanophenyl)-5-methyl-4-[3-(trifluoromethyl)phenyl]-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate (100 mg, 220 μmol) in an ethanol/THF/water mixture (4:1:0.6, 5.6 ml). The solution was heated at 55° C. for 1.5 h. At 0° C., the mixture was then acidified with 1 N hydrochloric acid (0.66 ml) and then directly purified by preparative HPLC (Kromasil C18 column; mobile phase: acetonitrile/water+0.1% TFA 10:90→90:10). The product was obtained as a colorless amorphous solid (67 mg, 71% of theory).

Workup

customAt 0° C.
customdirectly purified by preparative HPLC (Kromasil C18 column; mobile phase: acetonitrile/water+0.1% TFA 10:90→90:10)
customThe product was obtained as a colorless amorphous solid (67 mg, 71% of theory)

Sources & evidence

ORD record: ord-6385b750a14a4bf5851097ea3b8c08f3
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569314B2

Reaction notes

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