Dimethylformamide → (+/-)-2-Amino-7-(3,4-dimethoxy-3-methylbut-1-yn-1-yl)-1-ethyl-N-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxamide

HRID 210447Notes

Reaction equation

HRID 210447 reaction equation
[CH3:20][O:21][C:22]([C:23]#[CH:24])([CH2:25][O:26][CH3:27])[CH3:28].[CH3:34][CH2:35][N:36]([CH2:37][CH3:38])[CH2:39][CH3:40].[Cu:41][I:42].[NH2:1][c:2]1[n:3]([CH2:18][CH3:19])[c:4]2[n:5][c:6]([Cl:17])[cH:7][cH:8][c:9]2[c:10](=[O:16])[c:11]1[C:12](=[O:13])[NH:14][CH3:15].[O:29]=[CH:30][N:31]([CH3:32])[CH3:33].[Pd:43]([Cl:44])[Cl:45].[c:46]1([P:47]([c:48]2[cH:49][cH:50][cH:51][cH:52][cH:53]2)[c:54]2[cH:55][cH:56][cH:57][cH:58][cH:59]2)[cH:60][cH:61][cH:62][cH:63][cH:64]1.[c:65]1([P:66]([c:67]2[cH:68][cH:69][cH:70][cH:71][cH:72]2)[c:73]2[cH:74][cH:75][cH:76][cH:77][cH:78]2)[cH:79][cH:80][cH:81][cH:82][cH:83]1>>[NH2:1][c:2]1[n:3]([CH2:18][CH3:19])[c:4]2[n:5][c:6]([C:24]#[C:23][C:22]([O:21][CH3:20])([CH2:25][O:26][CH3:27])[CH3:28])[cH:7][cH:8][c:9]2[c:10](=[O:16])[c:11]1[C:12](=[O:13])[NH:14][CH3:15]

Participants

8

Reactant 7

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 11776Triphenylphosphine2×HCID 24290Palladium ChlorideHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 866423362-Amino-7-chloro-1-ethyl-N-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxamideHCID 86642359(+/-)-3,4-Dimethoxy-3-methylbut-1-yne

Product 1

HCID 25127281(+/-)-2-Amino-7-(3,4-dimethoxy-3-methylbut-1-yn-1-yl)-1-ethyl-N-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxamide

Sources & evidence

ORD record
ord-6b528f9e229a4d55bda7664daabc3a4c
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (6/10)

Reaction notes

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