Methanol → HCID 67285881, compound

HRID 445237Notes

Reaction equation

[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][N:7]([CH2:14][C:15]1[CH:40]=[CH:39][C:18]([CH2:19][N:20]2[CH:24]([C:25]([OH:27])=[O:26])[CH2:23][C:22]3([CH2:32][CH2:31][N:30]([CH:33]4[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]4)[CH2:29][CH2:28]3)[CH2:21]2)=[CH:17][CH:16]=1)[CH2:8][C:9]1[NH:10][CH:11]=[CH:12][N:13]=1.S(Cl)(Cl)=O.[CH3:45]O>>[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][N:7]([CH2:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:19][N:20]2[CH:24]([C:25]([O:27][CH3:45])=[O:26])[CH2:23][C:22]3([CH2:32][CH2:31][N:30]([CH:33]4[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]4)[CH2:29][CH2:28]3)[CH2:21]2)=[CH:39][CH:40]=1)[CH2:8][C:9]1[NH:13][CH:12]=[CH:11][N:10]=1

Participants

Reactant 3

HCID 887Methanol

HCID 24386Thionyl Chloride

HCID 67285368HCID 67285368, compound

Product 1

HCID 67285881HCID 67285881, compound

Conditions

Temperature: 60 °C

Procedure

The compound (102 mg) obtained in Example 5(1) was dissolved in methanol (1 mL) and, furthermore, thionyl chloride (0.25 mL) was added at 0° C. The reaction solution was stirred at 60° C. for 1 hour. The reaction solution was concentrated under reduced pressure and the residue was purified by silica gel chromatography (manufactured by Fuji Silysia Chemical Ltd., CHROMATOREX NH (trade name)) (dichloromethane:methanol=1:0→4:1) to obtain the title compound (96.4 mg) having the following physical properties.

Workup

concentrationThe reaction solution was concentrated under reduced pressure
customthe residue was purified by silica gel chromatography (manufactured by Fuji Silysia Chemical Ltd., CHROMATOREX NH (trade name)) (dichloromethane:methanol=1:0→4:1)

Sources & evidence

ORD record: ord-e85a94103c0d47b8a0948fab337b92bf
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08476290B2

Reaction notes

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