1,2-Dichloroethane → HCID 178423795, compound
Reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[C:13]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[CH:12]=[C:11]([C:21](O)=[O:22])[CH:10]=1.Cl.Cl.[NH:26]1[CH:30]=[N:29][C:28]([C@H:31]([NH2:33])[CH3:32])=[N:27]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C>CN(C)C=O>[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[C:13]([N:15]2[CH2:16][CH2:17][O:18][CH2:19][CH2:20]2)[CH:12]=[C:11]([C:21]([NH:33][C@@H:31]([C:28]2[N:29]=[CH:30][NH:26][N:27]=2)[CH3:32])=[O:22])[CH:10]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2′-fluoro-4′methyl-5-morpholin-4-ylbiphenyl-3-carboxylic acid (52.0 mg, 0.15 mmol) in N,N-dimethylformamide (1.0 mL) was added (1R)-1-(1H-1,2,4-triazol-3-yl)ethanamine dihydrochloride (30.1 mg, 0.16 mmol), EDC (36.8 mg, 0.19 mmol), HOBT (22.6 mg, 0.15 mmol) and diisopropylethylamine (0.10 mL, 0.59 mmol). After 16 h, the mixture was purified by reverse phase HPLC (C-18, 95% water/acetonitrile→25% water/acetonitrile with 0.1% trifluoroacetic acid) to give the title compound. HRMS 410.1990 (M+1).). 1H NMR (500 MHz, CD3OD): δ 9.37 (s, 1H); 7.86 (d, J=7.6 Hz, 2H); 7.67 (s, 1H); 7.45 (t, J=8.1 Hz, 1H); 7.13 (d, J=7.9 Hz, 1H); 7.07 (d, J=12.0 Hz, 1H); 5.52-5.47 (m, 1H); 4.00 (t, J=4.6 Hz, 4H); 3.52 (t, J=4.5 Hz, 4H); 2.40 (s, 3H); 1.79 (d, J=7.1 Hz, 3H).
Workup
- customthe mixture was purified by reverse phase HPLC (C-18, 95% water/acetonitrile→25% water/acetonitrile with 0.1% trifluoroacetic acid)
Sources & evidence
- ORD record
- ord-1a60489b7e1a4988b3ef9e5fc92c306c
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08247401B2
Reaction notes
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