N-[(3R,4S)-4-ethoxypyrrolidin-3-yl]-3,6-diethyl-5-(6-methoxy-2-methylpyridin-3-yl)pyrazin-2-amine → N-[(3R,4S)-4-ethoxypyrrolidin-3-yl]-3,6-diethyl-5-(4-methoxy-2-methylphenyl)pyrazin-2-amine
Reaction equation
C(O[C@H]1CNC[C@H]1NC1C(CC)=NC(C2C(C)=NC(OC)=CC=2)=C(CC)N=1)C.[CH2:29]([C:31]1[C:32]([NH:48][C@H:49]2[C@@H:53]([O:54][CH2:55][CH3:56])[CH2:52][N:51](C(OCC3C=CC=CC=3)=O)[CH2:50]2)=[N:33][C:34]([CH2:46][CH3:47])=[C:35]([C:37]2[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][C:38]=2[CH3:45])[N:36]=1)[CH3:30]>>[CH2:55]([O:54][C@H:53]1[CH2:52][NH:51][CH2:50][C@H:49]1[NH:48][C:32]1[C:31]([CH2:29][CH3:30])=[N:36][C:35]([C:37]2[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][C:38]=2[CH3:45])=[C:34]([CH2:46][CH3:47])[N:33]=1)[CH3:56]Participants
3
Reactant 2
Product 1
Procedure
Following the procedure for the preparation of N-[(3R,4S)-4-ethoxypyrrolidin-3-yl]-3,6-diethyl-5-(6-methoxy-2-methylpyridin-3-yl)pyrazin-2-amine but substituting benzyl (3R,4S)-3-{[3,6-diethyl-5-(4-methoxy-2-methylphenyl)pyrazin-2-yl]amino}-4-ethoxypyrrolidine-1-carboxylate provided the title compound as an amber oil. 1H NMR (CDCl3) δ 1.12, 1.30, 2.12, 2.46, 2.72, 2.92–3.14, 3.36, 3.52, 3.63–3.82, 3.84, 4.18–4.24, 4.71–4.86, 5.11–5.22, 6.78, 6.83, 7.09; IR (diffuse reflectance) 2970 (s), 2933 (s), 2875, 2835, 2493 (b), 2467 (b), 2439 (b), 2353, 2338 (w), 1568 (s), 1563, 1482 (s), 1397 (s), 1393, 1242 (s) cm−1 HRMS (ESI) calcd for C22H32N4O2+H1 385.2603. found 385.2603.
Sources & evidence
- ORD record
- ord-f52efa2f4433498f97130db3ecaf5c79
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07250418B2
Reaction notes
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