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

HRID 2153781Notes

Reaction equation

HRID 2153781 reaction equation
[CH3:30][N:31]([CH3:32])[CH:33]=[O:34].[CH3:35][CH2:36][N:37]([CH2:38][CH3:39])[CH2:40][CH3:41].[CH:20]1([C:23]([CH2:24][O:25][CH3:26])([C:27]#[CH:28])[OH:29])[CH2:21][CH2:22]1.[Cu:42][I:43].[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].[Pd:44]([Cl:45])[Cl:46].[c:47]1([P:48]([c:49]2[cH:50][cH:51][cH:52][cH:53][cH:54]2)[c:55]2[cH:56][cH:57][cH:58][cH:59][cH:60]2)[cH:61][cH:62][cH:63][cH:64][cH:65]1.[c:66]1([P:67]([c:68]2[cH:69][cH:70][cH:71][cH:72][cH:73]2)[c:74]2[cH:75][cH:76][cH:77][cH:78][cH:79]2)[cH:80][cH:81][cH:82][cH:83][cH:84]1>>[NH2:1][c:2]1[n:3]([CH2:18][CH3:19])[c:4]2[n:5][c:6]([C:28]#[C:27][C:23]([CH:20]3[CH2:21][CH2:22]3)([CH2:24][O:25][CH3:26])[OH:29])[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 80410057(+/-)-2-Cyclopropyl-1-methoxybut-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 67081342(+/-)-2-Amino-7-(3-cyclopropyl-3-hydroxy-4-methoxybut-1-yn-1-yl)-1-ethyl-N-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxamide

Sources & evidence

ORD record
ord-1914c22f9d4d41fabfa261cfc52135ff
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (4/10)

Reaction notes

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