HCID 178471580, compound → HCID 178508901, compound

HRID 2350908Notes

Reaction equation

HRID 2350908 reaction equation
C([NH:7][C:8]1[N:9]=[C:10]([OH:45])[C:11]2[CH2:17][CH:16]([CH2:18][N:19]([CH2:22][C:23]3[CH:44]=[CH:43][C:26]([C:27]([NH:29][C@H:30]([C:38]([O:40]CC)=[O:39])[CH2:31][CH2:32][C:33]([O:35]CC)=[O:34])=[O:28])=[CH:25][CH:24]=3)[CH:20]=[O:21])[CH2:15][NH:14][C:12]=2[N:13]=1)(=O)C(C)(C)C>[OH-].[Na+]>[NH2:7][C:8]1[N:9]=[C:10]([OH:45])[C:11]2[CH2:17][CH:16]([CH2:18][N:19]([CH2:22][C:23]3[CH:24]=[CH:25][C:26]([C:27]([NH:29][C@H:30]([C:38]([OH:40])=[O:39])[CH2:31][CH2:32][C:33]([OH:35])=[O:34])=[O:28])=[CH:43][CH:44]=3)[CH:20]=[O:21])[CH2:15][NH:14][C:12]=2[N:13]=1

Participants

3

Reactant 1

HCID 178471580HCID 178471580, compound

Product 1

HCID 178508901HCID 178508901, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 0.5 g, (0.8 mmol) of diethyl N-[N-(2-pivaloylamino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-ylmethyl)-N-formyl-4-aminomethylbenzoyl]-glutamate in 0.1N NaOH was stirred at 25° C. for 5 days. The reaction mixture was filtered and the filtrate rendered acidic (pH 4) with 0.5N hydrochloric acid. The solid which formed after 1 h at 0° C. was collected, washed with water, and dried over P2O5 to give 0.26 g (67% yield) of N-[N-(2-amino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-ylmethyl)-N-formyl-4-aminomethylbenzoyl]-glutamic acid. An analytical sample was recrystallized from ethanol; mp 178° C. with gradually decomposition; 1H NMR (Me2SO d6) delta 1.75-2.23 (m, 5H), 2.2-2.42 (m, 3H), 2.65.varies.2.83 (m, 1H), 3.0-3.17 (m, 2H), 4.36-4.40 (m, 1H), 4.44-4.60 (m, 2 H), 5.95 (s, 2H), 6.29 (s, 1H), 7.28-7.36 (m, 2H, AA'BB'), 7.69-7.92 (m, 2H, AA'BB'), 8.10 and 8.36 (s, 1H), 8.57 (t, 1H, J=7.78 Hz), 9.8 (br s, 1H). Anal. Calcd for C22H26N6O7 : C, 54.32; H, 5.39; N, 17.28. Found: C, 54.67; H, 5.46; N, 17.02.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customThe solid which formed after 1 h at 0° C.
  3. customwas collected
  4. washwashed with water
  5. dry with materialdried over P2O5

Sources & evidence

ORD record
ord-46ab4ef4a6db4e23a09c05279aaa717e
Source dataset
uspto-grants-1989_10
Patent number
US04871746

Reaction notes

Loading…