HCID 66782407, compound → HCID 66782284, compound

HRID 1096551Notes

Reaction equation

HRID 1096551 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([CH2:10][N:11]([CH2:44][CH:45](OCC)OCC)[C:12]([CH:14]([NH:27][C:28](=[O:43])[CH2:29][CH:30]([NH:32][C:33]([NH:35][CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[O:34])[CH3:31])[CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22]C(C)(C)C)=[CH:18][CH:17]=3)=[O:13])[C:4]=2[N:3]=[CH:2]1>C(O)=O>[CH2:36]([NH:35][C:33]([N:32]1[CH:30]([CH3:31])[CH2:29][C:28](=[O:43])[N:27]2[CH:14]([CH2:15][C:16]3[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=3)[C:12](=[O:13])[N:11]([CH2:10][C:9]3[C:4]4[N:3]=[CH:2][S:1][C:5]=4[CH:6]=[CH:7][CH:8]=3)[CH2:44][CH:45]12)=[O:34])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

3

Reactant 1

HCID 66782407HCID 66782407, compound

Product 1

HCID 66782284HCID 66782284, compoundYield 37.2%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of crude N-[1-[Benzothiazol-4-ylmethyl-(2,2-diethoxy-ethyl)-carbamoyl]-2-(4-tert-butoxy-phenyl)-ethyl]-3-(3-benzyl-ureido)-butyramide (3.55 g, 4.95 mmol) in formic acid (100 mL) was stirred at room temperature for 13 h. The solvent was removed under reduced pressure and then diluted with EtOAc, washed with water and brine. The organic layer was dried with Na2SO4 and concentrated in vacuo. The residue was purified by chromatography and recrystallized on ethyl acetate and hexane to give 8-Benzothiazol-4-ylmethyl-6-(4-hydroxy-benzyl)-2-methyl-4,7-dioxo-hexahydro-pyrazino[1,2-a]pyrimidine-1-carboxylic acid benzylamide (1.05 g, 3 step yield: 32%). 1H NMR (CDCl3, 300 MHz) δ 9.25 (s, 1H), 7.4˜7.26 (m, 3H), 7.2 (d, J=7.01, 2H), 6.98 (t, J=8.0, 1H), 6.85 (m, 3H), 6.8 (t, J=7.0, 1H), 6.5 (d, J=8.76, 2H), 5.6 (m, 1H), 5.25 (t, J=4.7, 1H), 4.55 (m, 1H), 4.5˜4.25 (m, 4H), 3.5˜3.3 (m, 2H), 3.25˜3.1 (m, 2H), 2.2 (t, J=7.2, 2H) 1.45 (m, 3H) MS ESI 570 (M+H), 592 (M+Na).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additiondiluted with EtOAc
  3. washwashed with water and brine
  4. dry with materialThe organic layer was dried with Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography
  7. customrecrystallized on ethyl acetate and hexane

Sources & evidence

ORD record
ord-aa9f9f67ccab40a0ac40ab4f85b8f9a4
Source dataset
uspto-grants-2012_03
Patent number
US08138337B2

Reaction notes

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