Oxan-3-amine hydrochloride → 2-(3,4,5-Trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (tetrahydro-pyran-3-yl)-amide

HRID 1677373Notes

Reaction equation

HRID 1677373 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[N:14]=[C:15]3[C:21]([C:22]([OH:24])=O)=[CH:20][NH:19][C:16]3=[N:17][CH:18]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].Cl.[O:26]1[CH2:31][CH2:30][CH2:29][CH:28]([NH2:32])[CH2:27]1>CN(C1C=CN=CC=1)C.C(N(CC)CC)C>[O:26]1[CH2:31][CH2:30][CH2:29][CH:28]([NH:32][C:22]([C:21]2[C:15]3[C:16](=[N:17][CH:18]=[C:13]([C:5]4[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=4)[N:14]=3)[NH:19][CH:20]=2)=[O:24])[CH2:27]1

Participants

5

Reactant 2

HCID 46735995Oxan-3-amine hydrochlorideHCID 595407962-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

Product 1

HCID 442074302-(3,4,5-Trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (tetrahydro-pyran-3-yl)-amide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8471TriethylamineSolvent

Procedure

2-(3,4,5-Trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (tetrahydro-pyran-3-yl)-amide was prepared starting from 2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid and tetrahydro-pyran-3-ylamine hydrochloride following the general procedures described in these Examples but with triethylamine and DMAP added. MP 191-192° C., M+H 413.

Workup

  1. additionadded

Sources & evidence

ORD record
ord-c6e1e9c0cbac436593dced3a8ab96abd
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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