Tert-Butylamine → HCID 10732632, compound

HRID 1653697Notes

Reaction equation

HRID 1653697 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([NH:11][C:12]2[C:13](=O)[C:14](=[O:19])[C:15]=2[O:16]CC)[CH:2]=1.[C:21]([NH2:25])([CH3:24])([CH3:23])[CH3:22]>C(O)C>[C:21]([NH:25][C:13]1[C:14](=[O:19])[C:15](=[O:16])[C:12]=1[NH:11][C:3]1[CH:2]=[N:1][C:10]2[C:5]([CH:4]=1)=[CH:6][CH:7]=[CH:8][CH:9]=2)([CH3:24])([CH3:23])[CH3:22]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 10706995HCID 10706995, compound

Product 1

HCID 10732632HCID 10732632, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To the product from Example 13, Step 1 (0.30 g, 1.12 mmol) in ethanol (8 mL) was added tert-butylamine (0.35 mL, 3.36 mmol) and the resulting mixture was heated at 60° C. overnight. The mixture was concentrated, and the residue was dissolved in ethylacetate. Addition of hexanes induced precipitation of product which was filtered and triturated with diethylether/hexanes. Filtration and drying afforded 0.28 g (85%) of the title compound as a yellow solid, three -quarter hydrate: mp 257°-260° C.; 1H NMR (DMSO-d6) d 10.00 (br d, 1H), 8.9 (d, 1H), 8.4 (m, 1H), 8.02 (d, 1H), 7.96 (br d, 1H), 7.86 (dd, 1H), 7.66-7.54 (m, 2H), 1.45 (s, 9H). IR (KBr) 3400, 3200, 2980, 1785, 1680cm-1 ; MS (m/z) 296 (MH+).

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionthe residue was dissolved in ethylacetate
  3. additionAddition of hexanes
  4. customprecipitation of product which
  5. filtrationwas filtered
  6. customtriturated with diethylether/hexanes
  7. filtrationFiltration
  8. customdrying

Sources & evidence

ORD record
ord-e6a3c52e55724f2691baaf1f14ae59f2
Source dataset
uspto-grants-1995_04
Patent number
US05403854

Reaction notes

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