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

HRID 1139059Notes

Reaction equation

HRID 1139059 reaction equation
[CH3:36][CH2:37][N:38]([CH2:39][CH3:40])[CH2:41][CH3:42].[Cu:43][I:44].[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:31]=[CH:32][N:33]([CH3:34])[CH3:35].[Pd:45]([Cl:46])[Cl:47].[c:48]1([P:49]([c:50]2[cH:51][cH:52][cH:53][cH:54][cH:55]2)[c:56]2[cH:57][cH:58][cH:59][cH:60][cH:61]2)[cH:62][cH:63][cH:64][cH:65][cH:66]1.[c:67]1([P:68]([c:69]2[cH:70][cH:71][cH:72][cH:73][cH:74]2)[c:75]2[cH:76][cH:77][cH:78][cH:79][cH:80]2)[cH:81][cH:82][cH:83][cH:84][cH:85]1.[n:20]1[c:21]([C:26]([CH3:27])([C:28]#[CH:29])[OH:30])[cH:22][n:23][cH:24][cH:25]1>>[NH2:1][c:2]1[n:3]([CH2:18][CH3:19])[c:4]2[n:5][c:6]([C:29]#[C:28][C:26]([c:21]3[n:20][cH:25][cH:24][n:23][cH:22]3)([CH3:27])[OH:30])[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 582214102-(Pyrazin-2-yl)but-3-yn-2-olHCID 866423362-Amino-7-chloro-1-ethyl-N-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxamide

Product 1

HCID 67081541(+/-)-2-Amino-1-ethyl-7-(3-hydroxy-3-pyrazin-2-ylbut-1-yn-1-yl)-N-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxamide

Sources & evidence

ORD record
ord-ae6f8b2c31bf4882bc449227c0790ff8
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (7/10)

Reaction notes

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