Triethylamine → HCID 131736619, compound

HRID 1481082Notes

Reaction equation

CO[C:3]([C:5]1[N:6]=[C:7]([C:25]#[N:26])[C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1OC)[CH:9]=2)=[O:4].[NH2:27][C@H:28]([CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C@@H:29]([OH:34])[C:30]([O:32][CH3:33])=[O:31].CCN(CC)CC>CO>[C:25]([C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[C:10]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:9]=2)[C:14]([OH:15])=[C:5]([C:3]([NH:27][C@H:28]([CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C@@H:29]([OH:34])[C:30]([O:32][CH3:33])=[O:31])=[O:4])[N:6]=1)#[N:26]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 1-cyano-4-hydroxy-7-(2-methoxy-phenoxy)-isoquinoline-3-carboxylic acid methyl ester (20 mg, 0.06 mmol), (2R,3R)-methyl 3-amino-2-hydroxy-4-phenylbutanoate (43 mg, 0.13 mmol) and Et3N (0.04 mL, 0.27 mmol) in MeOH (2 mL) was heated at 150° C. in a microwave for 3 hours. The solvent was removed in vacuo and the residue oil was purified by flash chromatography (0-10% EtOAc/CH2Cl2) to give the title compound in 7 mg. MS: (−) m/z 496.34 (M-1).

Workup

customThe solvent was removed in vacuo
customthe residue oil was purified by flash chromatography (0-10% EtOAc/CH2Cl2)

Sources & evidence

ORD record: ord-71e50d043f364218b033ae989320dcec
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409892B2

Reaction notes

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