Carbonochloridic acid, 2-fluoroethyl ester → 2-Fluoroethyl (cis)-3-{[5-(2,4-dichlorophenyl)-3,6-diethylpyrazin-2-yl]amino}-4-ethoxypyrrolidine-1-carboxylate
Reaction equation
C([N:4]1[CH2:8][C@H:7]([O:9][CH2:10][CH3:11])[C@H:6]([NH:12][C:13]2[C:18]([CH2:19][CH3:20])=[N:17][C:16]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=3[Cl:28])=[C:15]([CH2:29][CH3:30])[N:14]=2)[CH2:5]1)(=O)C.Cl[C:32]([O:34][CH2:35][CH2:36][F:37])=[O:33]>>[Cl:28][C:22]1[CH:23]=[C:24]([Cl:27])[CH:25]=[CH:26][C:21]=1[C:16]1[N:17]=[C:18]([CH2:19][CH3:20])[C:13]([NH:12][C@H:6]2[C@@H:7]([O:9][CH2:10][CH3:11])[CH2:8][N:4]([C:32]([O:34][CH2:35][CH2:36][F:37])=[O:33])[CH2:5]2)=[N:14][C:15]=1[CH2:29][CH3:30]Participants
3
Reactant 2
Product 1
Procedure
Following the procedure for the preparation of N-[(cis)-1-acetyl-4-ethoxypyrrolidin-3-yl]-5-(2,4-dichlorophenyl)-3,6-diethylpyrazin-2-amine but substituting 2-fluoroethyl chloroformate and making non-critical variations provided the title compound as an oil: 1H NMR (400 MHz, CDCl3) δ) 7.49, 7.34–7.26, 5.21, 4.70–4.58, 4.56, 4.42, 4.34, 4.10, 3.99, 3.75–3.30, 2.71, 2.47, 1.32–1.26, 1.15; IR (liq.) 2973 (s), 2347 (b), 2181 (w), 1709 (s), 1567 (s), 1553 (s), 1500 (s), 1470 (s), 1445 (s), 1426 (s), 1396 (s), 1347 (s), 1140 (s), 1103 (s), 1060 (s), cm−1 HRMS (FAB) calcd for C23H29Cl2FN4O3+H 499.1679, found 499.1673. Anal. Calcd for C23H29Cl2FN4O3: C, 55.32; H, 5.85; N, 11.22. Found: C, 55.20; H, 5.91; N, 10.95.
Sources & evidence
- ORD record
- ord-0366615912f14047a380e7694d2fa816
- Source dataset
- uspto-grants-2006_05
- Patent number
- US07041672B2
Reaction notes
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