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-[6-methoxy-2-(trifluoromethyl)pyridin-3-yl]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:51][C@H:52]2[C@@H:56]([O:57][CH2:58][CH3:59])[CH2:55][N:54](C(OCC3C=CC=CC=3)=O)[CH2:53]2)=[N:33][C:34]([CH2:49][CH3:50])=[C:35]([C:37]2[C:38]([C:45]([F:48])([F:47])[F:46])=[N:39][C:40]([O:43][CH3:44])=[CH:41][CH:42]=2)[N:36]=1)[CH3:30]>>[CH2:58]([O:57][C@H:56]1[CH2:55][NH:54][CH2:53][C@H:52]1[NH:51][C:32]1[C:31]([CH2:29][CH3:30])=[N:36][C:35]([C:37]2[C:38]([C:45]([F:48])([F:47])[F:46])=[N:39][C:40]([O:43][CH3:44])=[CH:41][CH:42]=2)=[C:34]([CH2:49][CH3:50])[N:33]=1)[CH3:59]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-[6-methoxy-2-(trifluoromethyl)pyridin-3-yl]pyrazin-2-yl}amino)-4-ethoxypyrrolidine-1-carboxylate provided the title compound as an amber oil. 1H NMR (CDCl3) δ 1.13, 1.28, 2.41, 2.69, 3.14, 3.37, 3.51, 3.66˜3.75, 4.04, 4.16, 4.69, 5.29, 6.96, 7.54; IR (liq.) 2975 (s), 2417 (b), 2177 (b), 2029 (w), 1923 (w), 1609 (s), 1565 (s), 1479 (s), 1400 (s), 1341 (s), 1278 (s), 1239 (s), 1192 (s), 1177 (s), 1138 (s) cm−1.
Sources & evidence
- ORD record
- ord-824378dbbcc240f5b9fd37434ee5084c
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07250418B2
Reaction notes
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