HCID 178471560, compound → HCID 178471572, compound

HRID 1639244

Reaction equation

HRID 1639244 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]([C:29]1[CH:50]=[CH:49][C:32]([C:33]([NH:35][C@H:36]([C:44]([O:46][CH2:47][CH3:48])=[O:45])[CH2:37][CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])=[O:34])=[CH:31][CH:30]=1)=[CH:10][C:11]1[CH:28]=[N:27][C:14]2[N:15]=[C:16]([NH:20][C:21](=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23])[N:17]=[C:18]([OH:19])[C:13]=2[CH:12]=1>C(O)(=O)C.CO.[Pt](=O)=O>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH:9]([C:29]1[CH:50]=[CH:49][C:32]([C:33]([NH:35][C@H:36]([C:44]([O:46][CH2:47][CH3:48])=[O:45])[CH2:37][CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])=[O:34])=[CH:31][CH:30]=1)[CH2:10][CH:11]1[CH2:28][NH:27][C:14]2[N:15]=[C:16]([NH:20][C:21](=[O:26])[C:22]([CH3:23])([CH3:25])[CH3:24])[N:17]=[C:18]([OH:19])[C:13]=2[CH2:12]1

Participants

5

Reactant 1

HCID 178471560HCID 178471560, compound

Product 1

HCID 178471572HCID 178471572, compoundYield 68%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A solution of 1.16 g (1.68 mm) of diethyl N-[4-{1-(tetrahydropyr-2-yloxy)-3-(2-pivaloylamino-4-hydroxypyrido[2,3-d]pyrimidin-6-yl)prop-2-en-2-yl}benzoyl]glutamate and 174 mg (20%) of amorphous platinum (IV) oxide in 150 ml of glacial acetic acid was hydrogenated for 10 hours at 50 psi. The reaction mixture was diluted with 50 ml of methanol and filtered through Celite. The filtrate was concentrated and diluted with ethyl acetate. The solid which formed after cooling for 15 hour was collected by filtration, washed with cold ethyl acetate and dried to give 700 mg (68%) of diethyl N-[4-{1-(tetrahydropyr-2-yloxy)-3-(2-pivaloylamino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl)prop-2-yl}benzoyl]glutamate. mp 183°-186° C. Analysis calculated for C36H51O9N5 : C, 61.95; H, 7.37; N, 10.04. Found: C, 62.00; H, 7.17; N, 9.83. NMR (CDCL3), delta, 1.23 (t, 3H, J=7 Hz), 1.26 (s, 9H), 1.32 (t, 3H, J=7 Hz), 2.26-2.82 (m, 9H), 2.06-2.12 (m, 2H), 2.26-2.38 (m, 1H), 2.43-2.58 (m, 2H), 2.62-2.83 (m, 1H), 2.84-3.10 (m, 2H) 3.12-3.21 and 2.32-3.40 (m, m, 1H), 3.41-3.52 (m, 2H), 3.68-3.92 (m, 2H), 4.13 (q, 2H, J=7 Hz), 4.25 (q, 2H, J=7 Hz), 4.44-4.63 (m, 2H, CH, NH), 4.78-4.84 (m, 1H) 7.02 (brd, 1H, NH, J=7.1 Hz), 7.29 (brs, NH), 7.31-7.37 (m, 2H), 7.75-7.78 (m, 2H), 11.20 (brs, NH).

Workup

  1. filtrationfiltered through Celite
  2. concentrationThe filtrate was concentrated
  3. additiondiluted with ethyl acetate
  4. customThe solid which formed
  5. temperatureafter cooling for 15 hour
  6. filtrationwas collected by filtration
  7. washwashed with cold ethyl acetate
  8. customdried

Sources & evidence

ORD record
ord-0d57ad2024c645e88bc41651ef1ffa03
Source dataset
uspto-grants-1989_11
Patent number
US04883799

Linked notes

Loading…