1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 71547493, compound
Reaction equation
[F:1][C:2]([F:9])([F:8])[CH2:3][CH2:4][C:5](O)=[O:6].O.OC1C2N=NNC=2C=CC=1.C(N=C=NCCCN(C)C)C.[F:32][C:33]([F:51])([F:50])[C:34]1[CH:35]=[CH:36][C:37]([NH:40][C@@H:41]2[CH2:49][N:44]3[CH2:45][CH2:46][NH:47][CH2:48][C@@H:43]3[CH2:42]2)=[N:38][CH:39]=1>ClCCl.CN(C)C=O>[F:1][C:2]([F:9])([F:8])[CH2:3][CH2:4][C:5]([N:47]1[CH2:46][CH2:45][N:44]2[CH2:49][C@@H:41]([NH:40][C:37]3[CH:36]=[CH:35][C:34]([C:33]([F:51])([F:32])[F:50])=[CH:39][N:38]=3)[CH2:42][C@H:43]2[CH2:48]1)=[O:6]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solutions of 4,4,4-trifluorobutanoic acid (99 mg, 0.7 mmol) and hydroxybenzotriazole hydrate (54 mg, 0.35 mmol) in dichloromethane (4 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (163 mg, 1.05 mmol) in dichloromethane (1 mL). After 5 minutes, a solution of Example 20 (200 mg, 0.7 mmol) in dimethylformamide (1.5 mL) was added. The mixture was stirred at room temperature for 3 days and then concentrated. The residue was purified by chromatography on silica gel (ethyl acetate/methanol=10:1) to give the title compound. 1H NMR(400 MHz, DMSO-d6) δ ppm 1.30 (m, 1H), 1.80-2.10 (m, 2H), 2.35-2.70 (m, 6H), 2.80-2.97 (m, 3H), 3.10 (m, 1H), 3.82-4.00 (m, 1H), 4.30 (m, 1H), 4.35-4.50 (m, 1H), 6.60 (d, 1H, J=7 Hz), 7.55 (m, 1H), 7.60 (d, 1H, J=7 Hz), 8.28 (s, 1H); MS (ESI) m/z 411 (M+H)+.
Workup
- concentrationconcentrated
- customThe residue was purified by chromatography on silica gel (ethyl acetate/methanol=10:1)
Sources & evidence
- ORD record
- ord-4880d74363794d519569defc544497d1
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08669255B2
Reaction notes
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