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

HRID 1824205Notes

Reaction equation

HRID 1824205 reaction equation
ClC1C=C(Cl)C=CC=1C1N=C(CC)C(N[C@@H]2C3C(=CC=CC=3)C[C@@H]2OCC)=NC=1CC.[CH2:32]([C:34]1[C:35]([NH:42][C@H:43]2[C@@H:47]([OH:48])[CH2:46][N:45]([C:49]([O:51][CH2:52][C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)=[O:50])[CH2:44]2)=[N:36][C:37]([CH2:40][CH3:41])=[CH:38][N:39]=1)[CH3:33].[F:59][CH2:60][CH2:61]Br>>[CH2:32]([C:34]1[C:35]([NH:42][C@H:43]2[C@@H:47]([O:48][CH2:61][CH2:60][F:59])[CH2:46][N:45]([C:49]([O:51][CH2:52][C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)=[O:50])[CH2:44]2)=[N:36][C:37]([CH2:40][CH3:41])=[CH:38][N:39]=1)[CH3:33]

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 60044796benzyl (3R,4S)-3-[(3,6-diethylpyrazin-2-yl)amino]-4-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 58583490benzyl(3R,4S)-3-[(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-[(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, DMSO-d6) δ) 7.61, 7.38–7.36, 5.85, 5.08, 4.52, 4.50, 4.38, 4.22, 3.75–3.40, 2.60, 2.53, 1.19–1.13; IR (liq.) 2970 (s), 2937 (s), 2340 (w), 2068 (w), 1996 (w), 1954 (w), 1705 (s), 1546 (s), 1499 (s), 1448 (s), 1422 (s), 1395 (s), 1351 (s), 1136 (s), 1107 (s), cm−1; HRMS (FAB) calcd for C22H29FN4O3+H 417.2302, found 417.2299.

Sources & evidence

ORD record
ord-ad594fbc62b24f40981bc25d6e8f82fb
Source dataset
uspto-grants-2006_05
Patent number
US07041672B2

Reaction notes

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