5-(2,4-dichlorophenyl)-N-[(cis)-4-ethoxypyrrolidin-3-yl]-3,6-diethylpyrazin-2-amine → 3,6-diethyl-N-[(3R,4S)-4-(2-fluoroethoxy)pyrrolidin-3-yl]pyrazin-2-amine

HRID 1612291Notes

Reaction equation

HRID 1612291 reaction equation
ClC1C=C(Cl)C=CC=1C1N=C(CC)C(N[C@H]2[C@@H](OCC)CNC2)=NC=1CC.[CH2:28]([C:30]1[C:31]([NH:38][C@H:39]2[C@@H:43]([O:44][CH2:45][CH2:46][F:47])[CH2:42][N:41](C(OCC3C=CC=CC=3)=O)[CH2:40]2)=[N:32][C:33]([CH2:36][CH3:37])=[CH:34][N:35]=1)[CH3:29]>>[CH2:28]([C:30]1[C:31]([NH:38][C@H:39]2[C@@H:43]([O:44][CH2:45][CH2:46][F:47])[CH2:42][NH:41][CH2:40]2)=[N:32][C:33]([CH2:36][CH3:37])=[CH:34][N:35]=1)[CH3:29]

Participants

3

Reactant 2

HCID 103098205-(2,4-dichlorophenyl)-N-[(cis)-4-ethoxypyrrolidin-3-yl]-3,6-diethylpyrazin-2-amineHCID 58583490benzyl(3R,4S)-3-[(3,6-diethylpyrazin-2-yl)amino]-4-(2-fluoroethoxy)pyrrolidine-1-carboxylate

Product 1

HCID 585833573,6-diethyl-N-[(3R,4S)-4-(2-fluoroethoxy)pyrrolidin-3-yl]pyrazin-2-amine

Procedure

Following the procedure for the preparation of 5-(2,4-dichlorophenyl)-N-[(cis)-4-ethoxypyrrolidin-3-yl]-3,6-diethylpyrazin-2-amine but substituting benzyl (3R,4S)-3-[(3,6-diethylpyrazin-2-yl)amino]-4-(2-fluoroethoxy)pyrrolidine-1-carboxylate and making non-critical variations provided the title compound as an oil: 1H NMR (400 MHz, CDCl3) δ) 7.65, 5.21, 4.64, 4.53, 4.07, 3.81-3.61, 3.40, 3.22, 3.14, 2.82, 2.62, 1.33-1.25; IR (liq.) 3437, 2969 (s), 2936 (s), 2874, 2348 (w), 1580 (s), 1546 (s), 1498 (s), 1464, 1449 (s), 1395, 1162, 1129, 1043 (s), 870, cm−1; HRMS (FAB) calcd for C14H23FN4O+H 283.1934, found 283.1928.

Sources & evidence

ORD record
ord-ec3a2540f0af45f4935b9b1bed7544e8
Source dataset
uspto-grants-2006_01
Patent number
US06992087B2

Reaction notes

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