Acetic Anhydride → HCID 69016915, compound

HRID 1455155Notes

Reaction equation

HRID 1455155 reaction equation
[C:1]([O:5][C:6](=[O:42])[NH:7][CH:8]([N:11]([CH:21]([C:25]1[N:30]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:29](=[O:38])[C:28]([C:39]#[N:40])=[C:27]([CH3:41])[N:26]=1)[CH:22]([CH3:24])[CH3:23])[C:12]([C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1)=[O:13])[CH2:9][CH3:10])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.[CH3:50][C:51](OC(C)=O)=[O:52]>CC(O)=O.C(Cl)Cl.[Pd]>[C:1]([O:5][C:6](=[O:42])[NH:7][CH:8]([N:11]([CH:21]([C:25]1[N:30]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:29](=[O:38])[C:28]([CH2:39][NH:40][C:51](=[O:52])[CH3:50])=[C:27]([CH3:41])[N:26]=1)[CH:22]([CH3:23])[CH3:24])[C:12]([C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1)=[O:13])[CH2:9][CH3:10])([CH3:3])([CH3:4])[CH3:2]

Participants

7

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 69018264HCID 69018264, compound

Product 1

HCID 69016915HCID 69016915, compoundYield 27%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of {1-[{1-[5-Cyano-3-benzyl-6-methyl-4-oxo-3,4-dihydro-pyrimidin-2-yl]-2-methyl-propyl}-(1-p-tolyl-methanoyl)-amino]-propyl}-carbamic acid tert-butyl ester (350 mg, 0.6 mMol) in HOAc (10 mL) was carefully added 10% Pd/C (150 mg). The reaction was hydrogenated under a balloon of H2 for 18 h at RT, filtered through a pad of Celite®, rinsed with HOAc and evaporated under vacuum. To the crude amine (˜34% pure by LCMS, MS (ES) m/e 576.4 (M+H)+) in CH2Cl2 (10 mL) was added with stirring Et3N (280 uL, 2 mMol) and Ac2O (114 uL, 1.2 mMol). After stirring at RT for 2 h the reaction was concentrated under vacuum, taken up in EtOAc, washed with 1 N Na2CO3, 1 N HCl, brine, dried (MgSO4), filtered and evaporated under vacuum. Purification by flash chromatography (80% EtOAc/hexane) gave the title compound (0.10 g, 27%) as an off-white solid: MS (ES) m/e 618.4 (M+H)+.

Workup

  1. filtrationfiltered through a pad of Celite®
  2. washrinsed with HOAc
  3. customevaporated under vacuum
  4. concentrationwas concentrated under vacuum
  5. washwashed with 1 N Na2CO3, 1 N HCl, brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated under vacuum
  9. customPurification by flash chromatography (80% EtOAc/hexane)

Sources & evidence

ORD record
ord-ffbc3d8616174780914d8dce4d5d289e
Source dataset
uspto-grants-2009_01
Patent number
US07482343B2

Reaction notes

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