Sodium Hydroxide → HCID 9801362, compound

HRID 1057507Notes

Reaction equation

HRID 1057507 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]([N:9]1[CH2:15][C:14]2[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=2[CH:12]([CH2:20][C:21]([O:23]C)=[O:22])[CH2:11][CH2:10]1)=[O:8].[CH3:25][CH:26]([N:28]=[C:29]=[O:30])[CH3:27].[OH-].[Na+]>C(OCC)(=O)C>[CH3:25][CH:26]([NH:28][C:29]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]([N:9]1[CH2:15][C:14]2[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=2[CH:12]([CH2:20][C:21]([OH:23])=[O:22])[CH2:11][CH2:10]1)=[O:8])=[O:30])[CH3:27]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 61277Isopropyl isocyanateHCID 69191919HCID 69191919, compound

Product 1

HCID 9801362HCID 9801362, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A solution of methyl 2-(2-(N-(4-aminobut-1-yl) carbamoyl)-1H,3H,4H-5H-benzo[e]azapin-5-yl)acetate and 2-propyl isocyanate (1 eq) in ethyl acetate (2 mL) was heated at 60° C. for 48 hrs. The solvent was removed in vacuo and the residue was dissolved in methanol (0.1M) and 1N sodium hydroxide (3 eq). The mixture was heated at 60° C. for 24 hrs. The product was purified by preparative HPLC as a white solid (TFA salt, 55.5 mg, 59%): EI-MS m/z 405 (M+H); 1H-NMR (400 MHz, MeOH-d4): 7.29-7.14 (m, 4H), 4.54 (q, J=15.0 Hz, 2H), 3.79 (m,1H), 3.66 (m, 1H), 3.54 (m, 2H), 3.15-3.06 (m, 4H), 2.84-2.79 (m, 1H), 2.74-2.68 (m, 1H), 2.05-2.00 (m, 1H), 1.62-1.58 (m, 1H), 1.40-1.38 (m, 4H), 1.1 (d, J=6.8 Hz, 6H).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in methanol (0.1M)
  3. customThe product was purified by preparative HPLC as a white solid (TFA salt, 55.5 mg, 59%)

Sources & evidence

ORD record
ord-141b7bc46cb94076be03055ee94e6070
Source dataset
uspto-grants-2003_02
Patent number
US06514964B1

Reaction notes

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