8-Chloro-(1,2,4)triazolo(4,3-a)pyrazine → 5-((1R)-2-(3-(([1,2,4]Triazolo[4,3-a]pyrazin-8-ylamino)methyl)-3-phenylpyrrolidin-1-yl)-1-hydroxyethyl)-4-methylisobenzofuran-1(3H)-one

HRID 515129Notes

Reaction equation

HRID 515129 reaction equation
Cl.[NH2:2][CH2:3][C:4]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:8][CH2:7][N:6]([CH2:9][C@@H:10]([C:12]2[CH:21]=[CH:20][C:15]3[C:16](=[O:19])[O:17][CH2:18][C:14]=3[C:13]=2[CH3:22])[OH:11])[CH2:5]1.Cl[C:30]1[C:31]2[N:32]([CH:36]=[N:37][N:38]=2)[CH:33]=[CH:34][N:35]=1>>[N:38]1[N:37]=[CH:36][N:32]2[CH:33]=[CH:34][N:35]=[C:30]([NH:2][CH2:3][C:4]3([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH2:8][CH2:7][N:6]([CH2:9][C@@H:10]([C:12]4[C:13]([CH3:22])=[C:14]5[C:15](=[CH:20][CH:21]=4)[C:16](=[O:19])[O:17][CH2:18]5)[OH:11])[CH2:5]3)[C:31]=12

Participants

3

Reactant 2

HCID 125826128-Chloro-(1,2,4)triazolo(4,3-a)pyrazineHCID 901905175-((1R)-2-(3-(aminomethyl)-3-phenylpyrrolidin-1-yl)-1-hydroxyethyl)-4-methylisobenzofuran-1(3H)-one hydrochloride2×

Product 1

HCID 715660255-((1R)-2-(3-(([1,2,4]Triazolo[4,3-a]pyrazin-8-ylamino)methyl)-3-phenylpyrrolidin-1-yl)-1-hydroxyethyl)-4-methylisobenzofuran-1(3H)-one

Procedure

5-((1R)-2-(3-(([1,2,4]Triazolo[4,3-a]pyrazin-8-ylamino)methyl)-3-phenylpyrrolidin-1-yl)-1-hydroxyethyl)-4-methylisobenzofuran-1(3H)-one was prepared in a similar fashion to that described for the synthesis of EXAMPLE 18 starting from 5-[(R)-2-[3-(Aminomethyl)-3-phenylpyrrolidin-1-yl]-1-hydroxyethyl}-4-methyl-2-benzofuran-1(3H)-one hydrochloride [INTERMEDIATE 15] and 8-chloro-[1,2,4]triazolo[4,3-a]pyrazine.

Sources & evidence

ORD record
ord-3d31b26159ff4db892208a5ca5d12b26
Source dataset
uspto-grants-2015_08
Patent number
US09108947B2

Reaction notes

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