Methanol → HCID 178448677, compound
Reaction equation
[C:1]([N:5]1[C:9](=[O:10])[CH2:8][CH:7]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH:18]([NH:22][S:23]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=3)(=[O:25])=[O:24])[C:19]([NH2:21])=O)=[CH:13][CH:12]=2)[S:6]1(=[O:37])=[O:36])([CH3:4])([CH3:3])[CH3:2].C([O-])(=[O:40])C.[K+].Cl.[NH2:44][CH2:45][C:46]([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=O.[CH3:54][OH:55]>>[F:33][C:32]([F:35])([F:34])[C:54]([OH:40])=[O:55].[C:1]([N:5]1[C:9](=[O:10])[CH2:8][CH:7]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH:18]([NH:22][S:23]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=3)(=[O:25])=[O:24])[C:19]3[NH:44][CH:45]=[C:46]([C:48]4[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=4)[N:21]=3)=[CH:13][CH:12]=2)[S:6]1(=[O:37])=[O:36])([CH3:3])([CH3:4])[CH3:2]Participants
5
Conditions
- Temperature
- 65 °C
Procedure
A solution of 4.22-C of Step 3 (80 mg, 0.13 mmol) and potassium acetate (0.5 mg, 0.51 mmol) in methanol (1.1 mL) was heated to 65° C. and treated with a solution of 2-amino-1-phenylethanone hydrochloride (44 mg, 0.26 mmol) in methanol (0.5 mL). The reaction mixture was heated at 65° C. for 16 h, cooled and the solid was filtered. The solid was washed with methanol and the filtrate concentrated to a crude solid which was purified by preparative LCMS to yield 4.22-D (43 mg, 51%). LCMS found for C31H32F3N4O5S2 (M+H)+: m/z=661.
Workup
- temperaturecooled
- filtrationthe solid was filtered
- washThe solid was washed with methanol
- concentrationthe filtrate concentrated to a crude solid which
- customwas purified by preparative LCMS
- customto yield 4.22-D (43 mg, 51%)
Sources & evidence
- ORD record
- ord-9fa27ff5897d479e873448ba4db149bb
- Source dataset
- uspto-grants-2006_11
- Patent number
- US07141596B2
Reaction notes
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