benzyl(3R,4S)-3-{[5-(2-chloro-4-methoxyphenyl)-3,6-diethylpyrazin-2-yl]amino}-4-ethoxypyrrolidine-1-carboxylate → 5-(2-chloro-4-methoxyphenyl)-N-[(3R,4S)-4-ethoxypyrrolidin-3-yl]-3,6-diethylpyrazin-2-amine

HRID 1297291Notes

Reaction equation

HRID 1297291 reaction equation
ClC1C=C(Cl)C=CC=1C1N=C(CC)C(N[C@H]2[C@@H](OCC)CNC2)=NC=1CC.[Cl:28][C:29]1[CH:34]=[C:33]([O:35][CH3:36])[CH:32]=[CH:31][C:30]=1[C:37]1[N:38]=[C:39]([CH2:64][CH3:65])[C:40]([NH:45][C@H:46]2[C@@H:50]([O:51][CH2:52][CH3:53])[CH2:49][N:48](C(OCC3C=CC=CC=3)=O)[CH2:47]2)=[N:41][C:42]=1[CH2:43][CH3:44]>>[Cl:28][C:29]1[CH:34]=[C:33]([O:35][CH3:36])[CH:32]=[CH:31][C:30]=1[C:37]1[N:38]=[C:39]([CH2:64][CH3:65])[C:40]([NH:45][C@H:46]2[C@@H:50]([O:51][CH2:52][CH3:53])[CH2:49][NH:48][CH2:47]2)=[N:41][C:42]=1[CH2:43][CH3:44]

Participants

3

Reactant 2

HCID 10152814benzyl(3R,4S)-3-{[5-(2-chloro-4-methoxyphenyl)-3,6-diethylpyrazin-2-yl]amino}-4-ethoxypyrrolidine-1-carboxylateHCID 103098205-(2,4-dichlorophenyl)-N-[(cis)-4-ethoxypyrrolidin-3-yl]-3,6-diethylpyrazin-2-amine

Product 1

HCID 102377515-(2-chloro-4-methoxyphenyl)-N-[(3R,4S)-4-ethoxypyrrolidin-3-yl]-3,6-diethylpyrazin-2-amine

Procedure

Following the procedure for the preparation of 5-(2,4-dichlorophenyl)-N-[(3R,4S)-4-ethoxypyrrolidin-3-yl]-3,6-diethylpyrazin-2-amine but substituting benzyl (3R,4S)-3-{[5-(2-chloro-4-methoxyphenyl)-3,6-diethylpyrazin-2-yl]amino}-4-ethoxypyrrolidine-1-carboxylate and making non-critical variations provided the title compound as an oil: 1H NMR (CDCl3) δ 1.15, 1.22–1.34, 2.45, 2.71, 2.89, 3.06, 3.22, 3.41, 3.51, 3.65, 3.85, 4.51, 5.32, 6.88, 7.02, 7.24; IR (liq.) 2971 (s), 2935, 2496 (w), 2446, 2402 (w), 2261 (w), 2072 (w), 1605, 1566 (s), 1483 (s), 1441, 1395, 1287 (s), 1230 (s), 1045 (s) cm−1 HRMS (ESI) calcd for C21H29N4O2Cl+H1 405.2057. found 405.2044.

Sources & evidence

ORD record
ord-d8686e67c01c4fb79bdac408c44f2d87
Source dataset
uspto-grants-2007_07
Patent number
US07250418B2

Reaction notes

Loading…