Triethylamine → HCID 11487017, compound

HRID 1833119Notes

Reaction equation

[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH:29]=[CH:30][CH:31]=1)[C:8]([C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=2)[C:13]([CH2:24][CH2:25][C:26]([OH:28])=O)=[CH:12][N:11]=1)=[O:9])([CH3:3])[CH3:2].C([N:34](CC)CC)C.ClC(OCC(C)C)=O.[OH-].N>C1COCC1>[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH:29]=[CH:30][CH:31]=1)[C:8]([C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=2)[C:13]([CH2:24][CH2:25][C:26]([NH2:34])=[O:28])=[CH:12][N:11]=1)=[O:9])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: -20 °C

Procedure

The above carboxylic acid (70.3 mg) was dissolved in 6 ml of THF. Then at −30° C., triethylamine (0.055 ml) was added followed by isobutyl chloroformate (0.034 ml). The mixture was stirred at −20° C. for 30 minutes. Then 30% ammonia hydroxide solution (0.15 ml) was added. The mixture was stirred at room temperature overnight and then purified through a reverse preparative HPLC to give 3-[1-(3-Isopropoxy-benzoyl)-6,7-dimethoxy-isoquinolin-4-yl]-propionamid as a fluffy solid (47.2 mg). ES-MS calcd for C24H26N2O5 (m/e) 422.5, obsd 423.4 (M+H).

Workup

stirringThe mixture was stirred at room temperature overnight
custompurified through a reverse preparative HPLC

Sources & evidence

ORD record: ord-969c466124de4d08a03b895e678bee85
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067529B2

Reaction notes

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