benzyl (3R,4S)-3-[(3,6-diethylpyrazin-2-yl)amino]-4-ethoxypyrrolidine-1-carboxylate → benzyl (3R,4S)-3-[(3,6-diethyl-5-iodopyrazin-2-yl)amino]-4-ethoxypyrrolidine-1-carboxylate
Reaction equation
[CH2:1]([C:3]1[C:4]([NH:12][C@H:13]2[C@@H:17]([O:18][CH2:19][CH3:20])[CH2:16][N:15]([C:21]([O:23][CH3:24])=[O:22])[CH2:14]2)=[N:5][C:6]([CH2:10][CH3:11])=[C:7]([I:9])[N:8]=1)[CH3:2].C(C1C(N[C@H]2[C@@H](OCC)CN(C(OC[C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)=O)C2)=NC(CC)=CN=1)C>>[CH2:1]([C:3]1[C:4]([NH:12][C@H:13]2[C@@H:17]([O:18][CH2:19][CH3:20])[CH2:16][N:15]([C:21]([O:23][CH2:24][C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)=[O:22])[CH2:14]2)=[N:5][C:6]([CH2:10][CH3:11])=[C:7]([I:9])[N:8]=1)[CH3:2]Participants
3
Reactant 2
Product 1
Procedure
Following the procedure for the preparation of methyl (3R,4S)-3-[(3,6-diethyl-5-iodopyrazin-2-yl)amino]-4-ethoxypyrrolidine-1-carboxylate but substituting benzyl (3R,4S)-3-[(3,6-diethylpyrazin-2-yl)amino]-4-ethoxypyrrolidine-1-carboxylate provided the title compound as an oil: 1H NMR (400 MHz, CDCl3) δ) 7.30–7.25, 5.06, 4.96, 4.53, 3.96, 3.86, 3.64–3.47, 3.35, 3.25–3.13, 2.68, 2.51, 1.20–1.12; IR (liq.) 2972, 2338 (w), 1949 (w), 1708 (s), 1554 (s), 1537 (s), 1475 (s), 1456 (s), 1447 (s), 1421 (s), 1394 (s), 1351 (s), 1165, 1126, 1097 (s) cm−1 HRMS (ESI) calcd for C22H29N4O3I+H1 25.1364. found 525.1359. Anal. Calcd for C22H29IN4O3: C, 50.39; H, 5.57; N, 10.68. Found: C, 50.48; H, 5.60; N, 10.44.
Sources & evidence
- ORD record
- ord-9daeca5470d4449b9f6b68dce79bb392
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07250418B2
Reaction notes
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