Water → HCID 86758622, compound

HRID 1019373Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:24](C(OC)=O)=[C:23]([C:29]3[CH:34]=[C:33]([O:35][CH3:36])[C:32]([O:37][CH3:38])=[C:31]([O:39][CH3:40])[CH:30]=3)[C:22]3[C:17](=[CH:18][C:19]([OH:43])=[C:20]([O:41][CH3:42])[CH:21]=3)[C:16]2=[O:44])=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:45](=[O:48])([O-])[O-].[K+].[K+].Cl.[N:52]1[CH:57]=[CH:56][CH:55]=[CH:54][C:53]=1[CH2:58]Cl.O.CN(C)[CH:63]=[O:64]>C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH:24]([O:64][CH3:63])[C:23]([C:29]3[CH:34]=[C:33]([O:35][CH3:36])[C:32]([O:37][CH3:38])=[C:31]([O:39][CH3:40])[CH:30]=3)=[C:22]3[C:17](=[CH:18][C:19]([O:43][CH2:58][C:53]4[CH:54]=[CH:55][CH:56]=[CH:57][N:52]=4)=[C:20]([O:41][CH3:42])[C:21]3=[C:45]=[O:48])[C:16]2=[O:44])=[CH:11][CH:10]=1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

Conditions

Temperature: 60 °C

Procedure

The compound obtained in Example 5 (200 mg) is dissolved in dimethyl formamide (20 ml), and thereto are added potassium carbonate (92 mg), and 2-picolyl chloride hydrochloride (55 mg). The mixture is stirred at 60° C. overnight, and thereto are added water and ethyl acetate. The ethyl acetate layer is separated, washed, dried, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (solvent, hexane:ethyl acetate=1:2) to give 2-[4-(tert-butoxycarbonylamino)phenyl]-6-methoxy-3-methoxy-carbonyl-7-(2-pyridylmethyloxy)-4-(3,4,5-trimethoxyphenyl)-1(2H)-isoquinolinone (207 mg).

Workup

customThe ethyl acetate layer is separated
washwashed
customdried
concentrationconcentrated under reduced pressure
customThe residue is purified by silica gel column chromatography (solvent, hexane:ethyl acetate=1:2)

Sources & evidence

ORD record: ord-fd0f95ffc0534ed4bdbc9a42e9e283ba
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06486155B1

Reaction notes

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