N-[(3R,4S)-4-ethoxypyrrolidin-3-yl]-3,6-diethyl-5-(6-methoxy-2-methylpyridin-3-yl)pyrazin-2-amine → HCID 58914568, compound

HRID 1297293Notes

Reaction equation

HRID 1297293 reaction equation
C(O[C@H]1CNC[C@H]1NC1C(CC)=NC(C2C(C)=NC(OC)=CC=2)=C(CC)N=1)C.[CH3:29][N:30]([CH3:67])[C:31]1[N:36]=[CH:35][C:34]([C:37]2[N:38]=[C:39]([CH2:64][CH3:65])[C:40]([NH:45][C@H:46]3[C@@H:50]([O:51][CH2:52][CH3:53])[CH2:49][N:48](C(OCC4C=CC=CC=4)=O)[CH2:47]3)=[N:41][C:42]=2[CH2:43][CH3:44])=[C:33]([CH3:66])[CH:32]=1>>[CH3:67][N:30]([CH3:29])[C:31]1[N:36]=[CH:35][C:34]([C:37]2[N:38]=[C:39]([CH2:64][CH3:65])[C:40]([NH:45][C@H:46]3[C@@H:50]([O:51][CH2:52][CH3:53])[CH2:49][NH:48][CH2:47]3)=[N:41][C:42]=2[CH2:43][CH3:44])=[C:33]([CH3:66])[CH:32]=1

Participants

3

Reactant 2

HCID 58914560N-[(3R,4S)-4-ethoxypyrrolidin-3-yl]-3,6-diethyl-5-(6-methoxy-2-methylpyridin-3-yl)pyrazin-2-amineHCID 58914572HCID 58914572, compound

Product 1

HCID 58914568HCID 58914568, compound

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-({5-[6-(dimethylamino)-4-methylpyridin-3-yl]-3,6-diethyl pyrazin-2-yl}amino)-4-ethoxypyrrolidine-1-carboxylate provided the title compound as an oil: 1H NMR (400 MHz, CDCl3) δ) 7.98, 6.45, 5.30, 4.51, 4.04, 3.67, 3.52, 3.43, 3.19, 3.12, 2.92, 2.69, 2.51, 2.11, 1.32–1.25, 1.15; IR (liq.) 2971 (s), 2933 (s), 2873 (s), 2345 (b), 1946 (w), 1607 (s), 1565 (s), 1516 (s), 1490 (s), 1395 (s), 1373, 1207, 1163, 1125, 1080 cm−1 HRMS (ESI) calcd for C22H34N6O+H1 399.2872. found 399.2877.

Sources & evidence

ORD record
ord-5316207459214f3086d9cc0644f8b581
Source dataset
uspto-grants-2007_07
Patent number
US07250418B2

Reaction notes

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