2-Fluoroethyl bromide → benzyl (3R,4S)-3-{[5-(2,4-dichlorophenyl)-3,6-diethylpyrazin-2-yl]amino}-4-(2-fluoroethoxy)pyrrolidine-1-carboxylate

HRID 1612287Notes

Reaction equation

HRID 1612287 reaction equation
ClC1C=C(Cl)C=CC=1C1N=C(CC)C(N[C@@H]2C3C(=CC=CC=3)C[C@@H]2OCC)=NC=1CC.[Cl:32][C:33]1[CH:38]=[C:37]([Cl:39])[CH:36]=[CH:35][C:34]=1[C:40]1[N:41]=[C:42]([CH2:65][CH3:66])[C:43]([NH:48][C@H:49]2[C@@H:53]([OH:54])[CH2:52][N:51]([C:55]([O:57][CH2:58][C:59]3[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=3)=[O:56])[CH2:50]2)=[N:44][C:45]=1[CH2:46][CH3:47].[F:67][CH2:68][CH2:69]Br>>[Cl:32][C:33]1[CH:38]=[C:37]([Cl:39])[CH:36]=[CH:35][C:34]=1[C:40]1[N:41]=[C:42]([CH2:65][CH3:66])[C:43]([NH:48][C@H:49]2[C@@H:53]([O:54][CH2:69][CH2:68][F:67])[CH2:52][N:51]([C:55]([O:57][CH2:58][C:59]3[CH:60]=[CH:61][CH:62]=[CH:63][CH:64]=3)=[O:56])[CH2:50]2)=[N:44][C:45]=1[CH2:46][CH3:47]

Participants

4

Reactant 3

HCID 129822-Fluoroethyl bromideHCID 102170735-(2,4-dichlorophenyl)-N-[(1R,2S)-2-ethoxy-2,3-dihydro-1H-inden-1-yl]-3,6-diethylpyrazin-2-amineHCID 58583263Benzyl(cis)-3-{[5-(2,4-dichlorophenyl)-3,6-diethylpyrazin-2-yl]amino}-4-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 10153010benzyl (3R,4S)-3-{[5-(2,4-dichlorophenyl)-3,6-diethylpyrazin-2-yl]amino}-4-(2-fluoroethoxy)pyrrolidine-1-carboxylate

Procedure

Following the procedure for the preparation of 5-(2,4-dichlorophenyl)-N-[(1R,2S)-2-ethoxy-2,3-dihydro-1H-inden-1-yl]-3,6-diethylpyrazin-2-amine but substituting benzyl (3R,4S)-3-{[5-(2,4-dichlorophenyl)-3,6-diethylpyrazin-2-yl]amino}-4-hydroxypyrrolidine-1-carboxylate and 2-fluoro-1-bromo ethane, and making non-critical variations provided the title compound as a oil: 1H NMR (400 MHz, CDCl3) δ) 7.49, 7.41-7.25, 5.18, 4.81, 4.67, 4.55, 4.17, 4.06, 3.80-3.62, 3.39-3.29, 2.69, 2.47, 1.28, 1.15; IR (diffuse reflectance) 2971, 2386 (w), 2350 (w), 2338 (w), 2039 (w), 2014 (w), 1710 (s), 1699 (s,b), 1569, 1499, 1467 (s), 1450, 1428, 1420, 1397, cm−1; HRMS (FAB) calcd for C28H31Cl2FN4O3+H 561.1835, found 561.1808.

Sources & evidence

ORD record
ord-8c3bfc61ff9f41ad8f680f4143aac7f8
Source dataset
uspto-grants-2006_01
Patent number
US06992087B2

Reaction notes

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