3-Bromopyridine → 5-(2,4-dichlorophenyl)-N-[(3R,4S)-4-ethoxy-1-pyridin-3-ylpyrrolidin-3-yl]-3,6-diethylpyrazin-2-amine

HRID 1297299Notes

Reaction equation

HRID 1297299 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[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](C3SC=CN=3)[CH2:19]2)=[N:13][C:14]=1[CH2:15][CH3:16].Br[C:34]1[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=1>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[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:34]3[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=3)[CH2:19]2)=[N:13][C:14]=1[CH2:15][CH3:16]

Participants

3

Reactant 2

HCID 122863-BromopyridineHCID 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 589145635-(2,4-dichlorophenyl)-N-[(3R,4S)-4-ethoxy-1-pyridin-3-ylpyrrolidin-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 substituting 3-bromo pyridine provided the title compound as an amporphous solid: 1H NMR (400 MHz, CDCl3) δ) 7.97, 7.51, 7.46, 7.33–7.28, 7.11, 5.31, 4.92, 4.31, 3.92, 3.85, 3.78–3.33, 2.73, 2.49, 1.35–1.29, 1.16; HRMS (ESI) calcd for C25H29N5OCl2+H1 486.1827. found 486.1834.

Sources & evidence

ORD record
ord-3458b55998dc4fc9b43e9221ec999d76
Source dataset
uspto-grants-2007_07
Patent number
US07250418B2

Reaction notes

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