benzyl (3R,4S)-3-{[5-(2,4-dichlorophenyl)-3,6-diethylpyrazin-2-yl]amino}-4-(2-fluoroethoxy)pyrrolidine-1-carboxylate → 5-(2,4-dichlorophenyl)-3,6-diethyl-N-[(3R,4S)-4-(2-fluoroethoxy)pyrrolidin-3-yl]pyrazin-2-amine
Reaction equation
ClC1C=C(Cl)C=CC=1C1N=C(CC)C(N[C@H]2[C@@H](OCC)CNC2)=NC=1CC.[Cl:28][C:29]1[CH:34]=[C:33]([Cl:35])[CH:32]=[CH:31][C:30]=1[C:36]1[N:37]=[C:38]([CH2:64][CH3:65])[C:39]([NH:44][C@H:45]2[C@@H:49]([O:50][CH2:51][CH2:52][F:53])[CH2:48][N:47](C(OCC3C=CC=CC=3)=O)[CH2:46]2)=[N:40][C:41]=1[CH2:42][CH3:43]>>[Cl:28][C:29]1[CH:34]=[C:33]([Cl:35])[CH:32]=[CH:31][C:30]=1[C:36]1[N:37]=[C:38]([CH2:64][CH3:65])[C:39]([NH:44][C@H:45]2[C@@H:49]([O:50][CH2:51][CH2:52][F:53])[CH2:48][NH:47][CH2:46]2)=[N:40][C:41]=1[CH2:42][CH3:43]Participants
3
Reactant 2
Product 1
Procedure
Following the procedure for the preparation of 5-(2,4-dichlorophenyl)-N-[(cis)-4-ethoxypyrrolidin-3-yl]-3,6-diethylpyrazin-2-amine but substituting benzyl(3R,4S)-3-{[5-(2,4-dichlorophenyl)-3,6-diethylpyrazin-2-yl]amino}-4-(2-fluoroethoxy)pyrrolidine-1-carboxylate and making non-critical variations provided the title compound as an oil: 1H NMR (400 MHz, CDCl3) δ) 7.49, 7.35–7.26, 5.38, 4.68–4.53, 4.11, 3.88, 3.80, 3.74, 3.46, 3.24–3.16, 2.93, 2.70, 2.62, 2.29, 2.00, 1.33–1.24, 1.15; IR (liq.) 2971 (s), 2936 (s), 2874, 2359 (w), 2342 (w), 1566 (s), 1552 (s), 1500 (s), 1470 (s), 1396 (s), 1200 (s), 1129 (s), 1102 (s), 1046 (s), 868, cm−1; HRMS (FAB) calcd for C20H25Cl2FN4O+H 427.1468, found 427.1474.
Sources & evidence
- ORD record
- ord-579c5cefc7eb44b585a6a49788474911
- Source dataset
- uspto-grants-2006_05
- Patent number
- US07041672B2
Reaction notes
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