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

HRID 1297296Notes

Reaction equation

HRID 1297296 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][O:30][C:31]1[C:36]([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])=[CH:35][CH:34]=[C:33]([O:66][CH3:67])[N:32]=1>>[CH3:29][O:30][C:31]1[C:36]([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])=[CH:35][CH:34]=[C:33]([O:66][CH3:67])[N: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 58914561benzyl (3R,4S)-3-{[5-(2,6-dimethoxypyridin-3-yl)-3,6-diethylpyrazin-2-yl]amino}-4-ethoxypyrrolidine-1-carboxylate

Product 1

HCID 589145715-(2,6-dimethoxypyridin-3-yl)-N-[(3R,4S)-4-ethoxypyrrolidin-3-yl]-3,6-diethylpyrazin-2-amine

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-(2,6-dimethoxypyridin-3-yl)-3,6-diethylpyrazin-2-yl]amino}-4-ethoxypyrrolidine-1-carboxylate provided the title compound as an amber oil. 1H NMR (400 MHz, CDCl3) δ) 7.53, 6.42, 5.29, 4.52, 4.04, 3.98, 3.92, 3.66, 3.51, 3.40, 3.21, 3.12, 2.91, 2.72, 2.48, 1.28, 1.18; IR (liq.) 2972, 2418 (w), 2184 (w), 2036 (w), 1993 (w), 1603, 1581 (s), 1564, 1477 (s), 1423, 1395, 1376 (s), 1313 (s), 1233, 1022 cm−1 HRMS (ESI) calcd for C21H31N5O3+H1 402.2505. found 402.2516.

Sources & evidence

ORD record
ord-f70135093c4b47ccaa1ed940732cde07
Source dataset
uspto-grants-2007_07
Patent number
US07250418B2

Reaction notes

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