Dimethylformamide → HCID 11186150, compound

HRID 2242895Notes

Reaction equation

[NH2:1][C:2]1[C:3]2[N:4]([N:11]=[C:12]([C:14]3[O:15][CH:16]=[CH:17][CH:18]=3)[N:13]=2)[CH:5]=[C:6](C(O)=O)[N:7]=1.[CH3:19][C:20]([OH:23])([CH3:22])[CH3:21].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C[N:42]([CH:44]=[O:45])C>>[C:20]([O:23][C:44](=[O:45])[NH:42][C:6]1[N:7]=[C:2]([NH2:1])[C:3]2[N:4]([N:11]=[C:12]([C:14]3[O:15][CH:16]=[CH:17][CH:18]=3)[N:13]=2)[CH:5]=1)([CH3:22])([CH3:21])[CH3:19]

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 6386tert-Butanol

HCID 199401P,P-Diphenylphosphinic azide

HCID 11402309HCID 11402309, compound

Product 1

HCID 11186150HCID 11186150, compoundYield 16%

Conditions

Temperature: 80 °C

Procedure

A mixture containing 8-amino-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyrazine-6-carboxylic acid (100 mg, 0.41 mmol; see Example 8 above), TEA (209 μL, 1.5 mmol), t-BuOH (1.5 mL) and diphenylphosphoryl azide (339 μl, 1.6 mmol) in DMF (1.5 ml) was heated (at around 80° C.) overnight. The solvent was removed in vacuo and the residue was purified by HPLC (C18, H2O:MeCN gradient) to afford the product as a yellow solid (20 mg, 16%). 1H NMR (300 MHz, CDCl3) δ 1.56 (s, 9H), 5.92 (br. s, 2H), 6.58 (dd, J=3.4, 1.8 Hz, 1H), 7.15 (dd, J=3.4, 0.8 Hz, 1H), 7.62 (dd J=1.8, 0.8 Hz, 1H), 8.61 (br. s, 1H). MS: m/z 317 [M+H]+.

Workup

customThe solvent was removed in vacuo
customthe residue was purified by HPLC (C18, H2O:MeCN gradient)

Sources & evidence

ORD record: ord-743d3f41151d497fa1192ee89a815e63
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07674791B2

Reaction notes

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