HCID 58777355, compound → HCID 54717460, compound

HRID 1726676Notes

Reaction equation

HRID 1726676 reaction equation
[N:1]([CH2:4][C@H:5]1[CH2:9][CH2:8][C:7](=[O:10])[N:6]1[C:11]1[CH:41]=[C:40]([F:42])[CH:39]=[CH:38][C:12]=1[CH2:13][NH:14][C:15]([C:17]1[N:18]=[C:19]2[N:24]([C:25](=[O:35])[C:26]=1[O:27]CC1C=CC=CC=1)[CH2:23][CH2:22][O:21][C:20]2([CH3:37])[CH3:36])=[O:16])=[N+]=[N-]>[Pd]>[NH2:1][CH2:4][C@H:5]1[CH2:9][CH2:8][C:7](=[O:10])[N:6]1[C:11]1[CH:41]=[C:40]([F:42])[CH:39]=[CH:38][C:12]=1[CH2:13][NH:14][C:15]([C:17]1[N:18]=[C:19]2[N:24]([C:25](=[O:35])[C:26]=1[OH:27])[CH2:23][CH2:22][O:21][C:20]2([CH3:37])[CH3:36])=[O:16]

Participants

3

Reactant 1

HCID 58777355HCID 58777355, compound

Product 1

HCID 54717460HCID 54717460, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The title compound can be prepared by hydrogenolysis (H2, 10% Pd—C) of intermediate 195, (R)—N-(2-(2-(azidomethyl)-5-oxopyrrolidin-1-yl)-4-fluorobenzyl)-3-(benzyloxy)-9,9-dimethyl-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carboxamide. 1H NMR (400 MHz, MeOD) δ ppm: 7.54 (1H, dd, J=7.0 Hz), 7.25-7.13 (2H, m), 4.62 (2H, m), 4.17 (1H, d, J=15.6 Hz), 4.07 (2H, m), 3.99 (2H, m,), 3.23 (2H, d, J=3.1 Hz), 2.79-2.59 (3H, m), 2.14 (1H, m), 1.66 (6H, s). HRMS calcd for C22H27N5O5F: 460.1996; found 460.2014.

Sources & evidence

ORD record
ord-87cf8e483f6b4db3ba70a000fcd8d603
Source dataset
uspto-grants-2009_02
Patent number
US07491819B1

Reaction notes

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