HCID 44539696, compound → HCID 44539698, compound

HRID 402571Notes

Reaction equation

HRID 402571 reaction equation
FC1C=CC(NCC2C(CO)=C(O)C(C([NH:18][OH:19])=O)=NC=2)=CC=1.[F:23][C:24]1[CH:46]=[CH:45][C:27]([CH2:28][CH2:29][NH:30][CH2:31][C:32]2[C:33]([CH2:43][OH:44])=[C:34]([OH:42])[C:35]([C:38](OC)=[O:39])=[N:36][CH:37]=2)=[CH:26][CH:25]=1>>[OH:19][NH:18][C:38]([C:35]1[C:34]([OH:42])=[C:33]([CH2:43][OH:44])[C:32]([CH2:31][NH:30][CH2:29][CH2:28][C:27]2[CH:45]=[CH:46][C:24]([F:23])=[CH:25][CH:26]=2)=[CH:37][N:36]=1)=[O:39]

Participants

3

Reactant 2

HCID 44539696HCID 44539696, compoundHCID 44540760HCID 44540760, compound2×

Product 1

HCID 44539698HCID 44539698, compound

Procedure

Product 22 was synthesized following a procedure similar to the one described above for the synthesis of 5-((4-fluorophenylamino)methyl)-N,3-dihydroxy-4-(hydroxymethyl)picolinamide starting from methyl 5-((4-fluorophenethylamino)methyl)-3-hydroxy-4-(hydroxymethyl)picolinate (compound 22b). 1H-NMR (500 MHz, DMSO-d6) δ ppm 8.08 (s, 1H), 7.24 (m, 2H), 7.09 (t, J=7.2 Hz, 2H), 4.58 (s, 2H), 3.92 (s, 2H), 2.80 (m, 2H), 2.76 (m, 2H). MS-ESI m/z 336 [MH]+

Sources & evidence

ORD record
ord-375e7240a92341899434e425f4a95526
Source dataset
uspto-grants-2014_06
Patent number
US08742123B2

Reaction notes

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