5-(2-chloro-4-methoxyphenyl)-N-[(3R,4S)-4-ethoxypyrrolidin-3-yl]-3,6-diethylpyrazin-2-amine → 5-(2-chloro-4-methoxyphenyl)-N-[(3R,4S)-4-ethoxy-1-(1,3-thiazol-2-yl)pyrrolidin-3-yl]-3,6-diethylpyrazin-2-amine

HRID 1297313Notes

Reaction equation

HRID 1297313 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]([CH2:31][CH3:32])[C:12]([NH:17][C@H:18]2[C@@H:22]([O:23][CH2:24][CH3:25])[CH2:21][N:20]([C:26]3[S:27][CH:28]=[CH:29][N:30]=3)[CH2:19]2)=[N:13][C:14]=1[CH2:15][CH3:16].ClC1C=[C:38]([O:40]C)C=CC=1C1N=C(CC)C(N[C@H]2[C@@H](OCC)CNC2)=NC=1CC>>[Cl:1][C:2]1[CH:7]=[C:6]([O:40][CH3:38])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]([CH2:31][CH3:32])[C:12]([NH:17][C@H:18]2[C@@H:22]([O:23][CH2:24][CH3:25])[CH2:21][N:20]([C:26]3[S:27][CH:28]=[CH:29][N:30]=3)[CH2:19]2)=[N:13][C:14]=1[CH2:15][CH3:16]

Participants

3

Reactant 2

HCID 102377515-(2-chloro-4-methoxyphenyl)-N-[(3R,4S)-4-ethoxypyrrolidin-3-yl]-3,6-diethylpyrazin-2-amineHCID 117851775-(2,4-dichlorophenyl)-N-[(3R,4S)-4-ethoxy-1-(1,3-thiazol-2-yl)pyrrolidin-3-yl]-3,6-diethylpyrazin-2-amine

Product 1

HCID 112717435-(2-chloro-4-methoxyphenyl)-N-[(3R,4S)-4-ethoxy-1-(1,3-thiazol-2-yl)pyrrolidin-3-yl]-3,6-diethylpyrazin-2-amine

Procedure

Following the procedure for the preparation of 5-(2,4-dichlorophenyl)-N-[(3R,4S)-4-ethoxy-1-(1,3-thiazol-2-yl)pyrrolidin-3-yl}-3,6-diethylpyrazin-2-amine but starting with 5-(2-chloro-4-methoxyphenyl)-N-[(3R,4S)-4-ethoxypyrrolidin-3-yl]-3,6-diethylpyrazin-2-amine provided the title compound as an amorphous solid. 1H NMR (CDCl3) δ 1.17, 1.25˜1.35, 2.50, 2.72, 3.45, 3.58, 3.75, 3.86, 4.04, 4.27, 4.93, 5.26, 6.55, 6.90, 7.02, 7.24; IR (diffuse reflectance) 2970, 2351 (w), 2337 (w), 2063 (w), 1604, 1568, 1549 (s), 1537 (s), 1482 (s), 1397, 1359, 1286, 1228, 1199, 1043 cm−1 HRMS (ESI) calcd for C24H30N5O2SCl+H1 488.1887. found 488.1880.

Sources & evidence

ORD record
ord-48bf7dc503984731b7b7f26a1865d746
Source dataset
uspto-grants-2007_07
Patent number
US07250418B2

Reaction notes

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