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

HRID 1824207Notes

Reaction equation

HRID 1824207 reaction equation
C(N1C[C@H](OCC)[C@H](NC2C(CC)=NC(C3C=CC(Cl)=CC=3Cl)=C(CC)N=2)C1)(=O)C.[CH2:31]([C:33]1[C:34]([NH:41][C@H:42]2[C@@H:46]([O:47][CH2:48][CH2:49][F:50])[CH2:45][NH:44][CH2:43]2)=[N:35][C:36]([CH2:39][CH3:40])=[CH:37][N:38]=1)[CH3:32].Cl[C:52]([O:54][CH3:55])=[O:53]>>[CH2:31]([C:33]1[C:34]([NH:41][C@H:42]2[C@@H:46]([O:47][CH2:48][CH2:49][F:50])[CH2:45][N:44]([C:52]([O:54][CH3:55])=[O:53])[CH2:43]2)=[N:35][C:36]([CH2:39][CH3:40])=[CH:37][N:38]=1)[CH3:32]

Participants

4

Reactant 3

HCID 6586Methyl chloroformateHCID 58583258N-[(cis)-1-acetyl-4-ethoxypyrrolidin-3-yl]-5-(2,4-dichlorophenyl)-3,6-diethylpyrazin-2-amineHCID 585833573,6-diethyl-N-[(3R,4S)-4-(2-fluoroethoxy)pyrrolidin-3-yl]pyrazin-2-amine

Product 1

HCID 58583295methyl(3R,4S)-3-[(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 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 (400 MHz, DMSO-d6) δ) 7.61, 5.82, 4.55, 4.51, 4.39, 4.19, 3.73–3.48, 2.64–2.49, 1.20–1.14; IR (diffuse reflectance) 2967, 2934, 2873, 2450 (w), 2407 (w), 2350 (w), 2334 (w), 2226 (w), 1699 (s), 1499, 1457 (s), 1392 (s), 1158, 1142, 768, cm−1; HRMS (FAB) calcd for C16H25FN4O3+H 341.1989, found 341.1988.

Sources & evidence

ORD record
ord-1968eb16d44b4b4a870a44fa5f2a2173
Source dataset
uspto-grants-2006_05
Patent number
US07041672B2

Reaction notes

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