Diisopropylethylamine → HCID 57849761, compound
Reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16]([OH:18])=[O:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C(ON1N=NC2[CH:30]=[CH:31][CH:32]=[N:33]C1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[CH2:52]([O:59][C:60](=[O:73])[C:61]1[CH:66]=[CH:65][C:64]([C:67]2[N:68]=[C:69]([NH2:72])[S:70][CH:71]=2)=[N:63][CH:62]=1)[C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1>CN(C=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16](=[O:18])[NH:72][C:69]1[S:70][CH:71]=[C:67]([C:64]2[CH:65]=[CH:66][C:61]([C:60](=[O:73])[NH:33][CH:32]3[CH2:30][CH2:31]3)=[CH:62][N:63]=2)[N:68]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[CH2:52]([O:59][C:60](=[O:73])[C:61]1[CH:66]=[CH:65][C:64]([C:67]2[N:68]=[C:69]([NH:72][C:16]([C@@H:12]3[CH2:13][CH2:14][CH2:15][N:11]3[C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:10])=[O:17])[S:70][CH:71]=2)=[N:63][CH:62]=1)[C:53]1[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=1Participants
7
Reactant 4
Product 2
Reagents, catalysts & solvents 1
Procedure
A mixture of (S)-Pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester (0.38 g, 1.52 mmol), HATU (0.58 g, 1.52 mmol)), and DIEA (0.4 mL, 3.0 mmol) in DMF (16 mL) was stirred at room temperature for 1 h. 6-(2-Amino-thiazol-4-yl)-nicotinic acid benzyl ester (0.32 g, 1.0 mmol) was added and the reaction mixture was heated to 50° C. for 48 h. The crude product was purified by reverse phase HPLC to furnish the desired product 6-{2-[((S)-1-Benzyloxycarbonyl-pyrrolidine-2-carbonyl)-amino]-thiazol-4-yl}-nicotinic acid benzyl ester.
Workup
- temperaturethe reaction mixture was heated to 50° C. for 48 h
- customThe crude product was purified by reverse phase HPLC
Sources & evidence
- ORD record
- ord-70635dc3b73d46bc91ed116dd182ba4d
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07595398B2
Reaction notes
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