Potassium Carbonate → Formate

HRID 1958827Notes

Reaction equation

[C:1]([NH:8][CH2:9][CH2:10]Br)([O:3]C(C)(C)C)=[O:2].[CH2:12]([C:14]1[CH:19]=[C:18]([C:20]2[N:24]=[C:23]([C:25]3[CH:30]=[C:29]([CH3:31])[CH:28]=[C:27]([CH2:32][N:33]([CH2:35][CH3:36])[CH3:34])[CH:26]=3)[O:22][N:21]=2)[CH:17]=[C:16]([CH3:37])[C:15]=1[OH:38])C.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH2:35]([N:33]([CH2:32][C:27]1[CH:26]=[C:25]([C:23]2[O:22][N:21]=[C:20]([C:18]3[CH:17]=[C:16]([CH3:37])[C:15]([O:38][CH2:10][CH2:9][NH2:8])=[C:14]([CH3:12])[CH:19]=3)[N:24]=2)[CH:30]=[C:29]([CH3:31])[CH:28]=1)[CH3:34])[CH3:36].[CH:1]([O-:3])=[O:2]

Participants

Conditions

Temperature: 70 °C

Procedure

2-(Boc-amino)-ethylbromide (66 mg, 285 μmol) was added to a suspension of 2-ethyl-4-(5-{3-[(ethyl-methyl-amino)-methyl]-5-methyl-phenyl}-[1,2,4]oxadiazol-3-yl)-6-methyl-phenol (52 mg, 142 μmol) and K2CO3 (60 mg, 427 μmol) in acetonitrile (2 mL). The mixture was stirred at 70° C. for 16 h before it was filtered. The filtrate was concentrated, dissolved in DCM (1 mL) and TFA (1 mL) and stirred at rt for 10 min. The mixture was again concentrated in vacuo and the crude product was purified by prep. HPLC to give the title compound as a formate salt in the form of a white lyophilisate (40 mg). LC-MS: tR=0.47 min; [M+1]+=409.30; 1H NMR (D6-DMSO): δ 1.06 (t, J=7.0 Hz, 3H), 1.26 (t, J=7.5 Hz, 3H), 2.16 (s, 3H), 2.38 (s, 3H), 2.43-2.48 (m, 5H), 2.75 (q, J=7.5 Hz, 2H), 3.26 (t, J=5.0 Hz, 2H), 3.56 (s, 2H), 3.99 (t, J=5.0 Hz, 2H), 7.48 (s, 1H), 7.83 (s, 2H), 7.91 (s, 1H), 7.93 (s, 1H), 8.17 (s, 2H, formate).

Workup

filtrationwas filtered
concentrationThe filtrate was concentrated
dissolutiondissolved in DCM (1 mL)
stirringTFA (1 mL) and stirred at rt for 10 min
concentrationThe mixture was again concentrated in vacuo
customthe crude product was purified by prep

Sources & evidence

ORD record: ord-32de037e90c14690895e674495b49aba
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410151B2

Reaction notes

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