HCID 57955593, compound → HCID 25254940, compound

HRID 914132Notes

Reaction equation

HRID 914132 reaction equation
[CH:1]1([N:7]2[CH2:13][C:12]([F:15])([F:14])[C:11](=[O:16])[N:10]([CH3:17])[C:9]3[CH:18]=[N:19][C:20]([NH:22][C:23]4[CH:47]=[CH:46][C:26]([C:27]([NH:29][N:30]5[CH2:35][CH2:34][N:33](C(OCC6C=CC=CC=6)=O)[CH2:32][CH2:31]5)=[O:28])=[CH:25][C:24]=4[O:48][CH3:49])=[N:21][C:8]2=3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>C(O)C.[Pd]>[CH:1]1([N:7]2[CH2:13][C:12]([F:15])([F:14])[C:11](=[O:16])[N:10]([CH3:17])[C:9]3[CH:18]=[N:19][C:20]([NH:22][C:23]4[CH:47]=[CH:46][C:26]([C:27]([NH:29][N:30]5[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]5)=[O:28])=[CH:25][C:24]=4[O:48][CH3:49])=[N:21][C:8]2=3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 1

HCID 57955593HCID 57955593, compound

Product 1

HCID 25254940HCID 25254940, compoundYield 92.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Benzyl 4-(4-(9-cyclohexyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxybenzamido)piperazine-1-carboxylate (850 mg, 1.25 mmols) was dissolved in ethanol (15 mL), added 10% Pd—C (170 mg, 20% wt) under inert atmosphere and hydrogenated using a balloon for 8 hrs. Then filtered the solution through celite bed and evaporated to give the product (630 mg). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.12-1.89 (m, 10H) 2.70-2.85 (m, 8H) 3.31 (s, 3H) 3.93 (s, 3H) 4.06 (t, J=13.26 Hz, 2H) 4.46 (m, 1H) 7.42 (d, J=8.0 Hz, 1H) 7.44 (s, 1H) 7.90 (s, 1H) 8.21 (s, 1H) 8.26 (d, J=8.08 Hz, 1H) 9.38 (s, 1H). [M+H] calculated for C26H34F2N8O3, 545. found 545.

Workup

  1. customfor 8 hrs
  2. filtrationThen filtered the solution through celite bed
  3. customevaporated

Sources & evidence

ORD record
ord-6130b90d334845a9bd512d54cdee5bbf
Source dataset
uspto-grants-2011_09
Patent number
US08026234B2

Reaction notes

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