Diisopropylethylamine → HCID 90308856, compound

HRID 2283667Notes

Reaction equation

[C:1]([O:5][C:6](=[O:15])[NH:7][C@@H:8]1[C@H:13]([NH2:14])[CH2:12][CH2:11][O:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.Cl[C:26]1[N:27]=[N:28][C:29]([C:42]([O:44][CH2:45][CH3:46])=[O:43])=[C:30]([NH:32][C:33]2[C:41]3[CH:40]=[CH:39][S:38][C:37]=3[CH:36]=[CH:35][CH:34]=2)[N:31]=1>C1COCC1>[S:38]1[CH:39]=[CH:40][C:41]2[C:33]([NH:32][C:30]3[N:31]=[C:26]([NH:14][C@@H:13]4[CH2:12][CH2:11][O:10][CH2:9][C@@H:8]4[NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:15])[N:27]=[N:28][C:29]=3[C:42]([O:44][CH2:45][CH3:46])=[O:43])=[CH:34][CH:35]=[CH:36][C:37]1=2

Participants

Conditions

Temperature: 80 °C

Procedure

Tert-butyl((3R,4R)-4-aminotetrahydro-2H-pyran-3-yl)carbamate (26 mg) and diisopropylethylamine (0.050 ml) were added to a solution of ethyl 3-chloro-5-(benzo[b]thiophen-4-ylamino)-1,2,4-triazine-6-carboxylate obtained in the above-described Step 1 (34 mg) in THF (1 mL), and the reaction solution was stirred at 80° C. for 30 minutes. The solvent was evaporated under vacuum, and the resultant residue was purified by column chromatography on silica gel (developing solvent:hexane-ethyl acetate) to obtain ethyl 5-(benzo[b]thiophen-4-ylamino)-3-((3R,4R)-3-(tert-butoxycarbonylamino)tetrahydro-2H-pyran-4-ylamino)-1,2,4-triazine-6-carboxylate.

Workup

customThe solvent was evaporated under vacuum
customthe resultant residue was purified by column chromatography on silica gel (developing solvent:hexane-ethyl acetate)

Sources & evidence

ORD record: ord-93eac45018a1406ebd07e8cdf1e32397
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145414B2

Reaction notes

Loading…