Dimethylformamide → (+/-)-2-Amino-1-ethyl-7-[(3-hydroxytetrahydrofuran-3-yl)ethynyl]-N-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxamide

HRID 1144946Notes

Reaction equation

HRID 1144946 reaction equation
[C:20](#[CH:21])[C:22]1([OH:27])[CH2:23][O:24][CH2:25][CH2:26]1.[CH2:28]([N:29]([CH2:30][CH3:31])[CH2:32][CH3:33])[CH3:34].[CH3:35][N:36]([CH3:37])[CH:38]=[O:39].[Cu:40][I:41].[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:42]([Cl:43])[Cl:44].[c:45]1([P:46]([c:47]2[cH:48][cH:49][cH:50][cH:51][cH:52]2)[c:53]2[cH:54][cH:55][cH:56][cH:57][cH:58]2)[cH:59][cH:60][cH:61][cH:62][cH:63]1.[c:64]1([P:65]([c:66]2[cH:67][cH:68][cH:69][cH:70][cH:71]2)[c:72]2[cH:73][cH:74][cH:75][cH:76][cH:77]2)[cH:78][cH:79][cH:80][cH:81][cH:82]1>>[NH2:1][c:2]1[n:3]([CH2:18][CH3:19])[c:4]2[n:5][c:6]([C:21]#[C:20][C:22]3([OH:27])[CH2:23][O:24][CH2:25][CH2:26]3)[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 156999173-Ethynyloxolan-3-olHCID 866423362-Amino-7-chloro-1-ethyl-N-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxamide

Product 1

HCID 67081591(+/-)-2-Amino-1-ethyl-7-[(3-hydroxytetrahydrofuran-3-yl)ethynyl]-N-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxamide

Sources & evidence

ORD record
ord-3f270bf1aa694197af47f668c1b22c6c
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (7/10)

Reaction notes

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