Methyl chloroformate → methyl(3R,4S)-3-{[5-(2-chloro-4-methoxyphenyl)-3,6-diethylpyrazin-2-yl]amino}-4-(2-fluoroethoxy)pyrrolidine-1-carboxylate

HRID 1612299Notes

Reaction equation

HRID 1612299 reaction equation
C(N1C[C@H](OCC)[C@H](NC2C(CC)=NC(C3C=CC(Cl)=CC=3Cl)=C(CC)N=2)C1)(=O)C.[Cl:31][C:32]1[CH:37]=[C:36]([O:38][CH3:39])[CH:35]=[CH:34][C:33]=1[C:40]1[N:41]=[C:42]([CH2:58][CH3:59])[C:43]([NH:48][C@H:49]2[C@@H:53]([O:54][CH2:55][CH2:56][F:57])[CH2:52][NH:51][CH2:50]2)=[N:44][C:45]=1[CH2:46][CH3:47].Cl[C:61]([O:63][CH3:64])=[O:62]>>[Cl:31][C:32]1[CH:37]=[C:36]([O:38][CH3:39])[CH:35]=[CH:34][C:33]=1[C:40]1[N:41]=[C:42]([CH2:58][CH3:59])[C:43]([NH:48][C@H:49]2[C@@H:53]([O:54][CH2:55][CH2:56][F:57])[CH2:52][N:51]([C:61]([O:63][CH3:64])=[O:62])[CH2:50]2)=[N:44][C:45]=1[CH2:46][CH3:47]

Participants

4

Reactant 3

HCID 6586Methyl chloroformateHCID 102380335-(2-chloro-4-methoxyphenyl)-3,6-diethyl-N-[(3R,4S)-4-(2-fluoroethoxy)pyrrolidin-3-yl]pyrazin-2-amineHCID 58583258N-[(cis)-1-acetyl-4-ethoxypyrrolidin-3-yl]-5-(2,4-dichlorophenyl)-3,6-diethylpyrazin-2-amine

Product 1

HCID 10311004methyl(3R,4S)-3-{[5-(2-chloro-4-methoxyphenyl)-3,6-diethylpyrazin-2-yl]amino}-4-(2-fluoroethoxy)pyrrolidine-1-carboxylate

Procedure

Following the procedure for the preparation of N-[(cis)-1-acetyl-4-ethoxypyrrolidin-3-yl]-5-(2,4-dichlorophenyl)-3,6-diethylpyrazin-2-amine but substituting 5-(2-chloro-4-methoxyphenyl)-3,6-diethyl-N-[(3R,4S)-4-(2-fluoroethoxy)pyrrolidin-3-yl]pyrazin-2-amine and methyl chloroformate, and making non-critical variations provided the title compound as an oil: 1H NMR (DMSO-d6) δ) 1.08, 1.15, 2.37, 2.65, 3.54, 3.60, 3.71, 3.82, 4.25, 4.43, 4.54, 5.93, 6.98, 7.10, 7.26; IR (liq.) 2972, 2068 (w), 1996 (w), 1707 (s), 1607, 1566, 1484 (s), 1454 (s), 1393 (s), 1287, 1230, 1197, 1175, 1128, 1104, cm−1 HRMS (FAB) calcd for C23H31ClN4O4+H 463.2112, found 463.2104.

Sources & evidence

ORD record
ord-136c40a4cd6d416ab9219b07ebeca29f
Source dataset
uspto-grants-2006_01
Patent number
US06992087B2

Reaction notes

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