N-[(3R,4S)-4-ethoxy-1-pyrimidin-2-ylpyrrolidin-3-yl]-3,6-diethyl-5-(6-methoxy-2-methylpyridin-3-yl)pyrazin-2-amine → 5-[6-(dimethylamino)-4-methylpyridin-3-yl]-N-[(3R,4S)-4-ethoxy-1-pyrimidin-2-ylpyrrolidin-3-yl]-3,6-diethylpyrazin-2-amine
Reaction equation
C(O[C@H]1CN([C:9]2[N:14]=[CH:13][CH:12]=[CH:11][N:10]=2)C[C@H]1NC1C(CC)=NC(C2C(C)=NC(OC)=CC=2)=C(CC)N=1)C.[CH3:35][N:36]([CH3:63])[C:37]1[N:42]=[CH:41][C:40]([C:43]2[N:44]=[C:45]([CH2:60][CH3:61])[C:46]([NH:51][C@H:52]3[C@@H:56]([O:57][CH2:58][CH3:59])[CH2:55][NH:54][CH2:53]3)=[N:47][C:48]=2[CH2:49][CH3:50])=[C:39]([CH3:62])[CH:38]=1>>[CH3:63][N:36]([CH3:35])[C:37]1[N:42]=[CH:41][C:40]([C:43]2[N:44]=[C:45]([CH2:60][CH3:61])[C:46]([NH:51][C@H:52]3[C@@H:56]([O:57][CH2:58][CH3:59])[CH2:55][N:54]([C:9]4[N:14]=[CH:13][CH:12]=[CH:11][N:10]=4)[CH2:53]3)=[N:47][C:48]=2[CH2:49][CH3:50])=[C:39]([CH3:62])[CH:38]=1Participants
3
Reactant 2
Product 1
Procedure
Following the procedure for the preparation of N-[(3R,4S)-4-ethoxy-1-pyrimidin-2-ylpyrrolidin-3-yl]-3,6-diethyl-5-(6-methoxy-2-methylpyridin-3-yl)pyrazin-2-amine but substituting 5-[6-(dimethylamino)-4-methylpyridin-3-yl]-N-[(3R,4S)-4-ethoxypyrrolidin-3-yl]-3,6-diethylpyrazin-2-amine provided the title compound as an amporphous solid: 1H NMR (400 MHz, CDCl3) δ) 8.36, 7.99, 6.53, 6.46, 5.19, 4.91, 4.22, 3.95, 3.73, 3.58–3.44, 3.13, 2.71, 2.54, 2.12, 1.32–1.26, 1.16; IR (diffuse reflectance) 2969, 2931, 2403 (w), 2351 (w), 2306 (w), 2212 (w), 2168 (w), 1606 (s), 1583 (s), 1568 (b), 1547 (s), 1508 (s), 1474 (s), 1393 (s), 798 cm−1 HRMS (ESI) calcd for C26H36N8O+H1 477.3090. found 477.3113.
Sources & evidence
- ORD record
- ord-f0940943294545d3bfe94d12096a0e2a
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07250418B2
Reaction notes
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