Water → HCID 58626007, compound

HRID 131366Notes

Reaction equation

HRID 131366 reaction equation
[NH2:1][CH:2]1[C:8](=[O:9])[NH:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[NH:4][C:3]1=[O:14].C(N(CC)CC)C.[C:22](Cl)(=[O:26])[CH:23]([CH3:25])[CH3:24].O>C1COCC1>[O:9]=[C:8]1[NH:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[NH:4][C:3](=[O:14])[CH:2]1[NH:1][C:22](=[O:26])[CH:23]([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 62325Isobutyryl chlorideHCID 219558063-amino-1H-1,5-benzodiazepine-2,4(3H,5H)-dione

Product 1

HCID 58626007HCID 58626007, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
1.5 °C

Procedure

Stir 3-amino-1,5-dihydro-benzo[b][1,4]diazepine-2,4-dione (10.0 g, 52.3 mmol) as a tan colored slurry in THF (300 mL) at 0-3° C. under nitrogen. Add triethylamine (8.00 mL, 57.0 mmol) in one portion. Add dropwise isobutyryl chloride (6.00 mL, 57.0 mmol) keeping the temperature below 3° C. Stir the resulting light yellow colored slurry at 0-3° C. for 3.5 hours until complete reaction by HPLC. Add deionized water (450 mL) over 15-20 minutes, keeping the pot temperature below 10° C. After stirring at 0-10° C. for 1.5 hours, isolate the product by filtration, rinse with cold (0-3° C.) 2:1/Water:THF (50 mL), then water (50 mL). Dry the solid in a vacuum oven at 50° C. to afford 10.5 g (77%) of the title compound: 1H NMR (500 MHz, DMSO-d6) δ 10.7 (s, 2H), 8.15 (d, 1H), 7.2 (m, 4H), 4.7 (d, 1H), 2.75 (m, 1H), 1.0 (s, 6H).

Workup

  1. customthe temperature below 3° C
  2. customuntil complete reaction by HPLC
  3. customthe pot temperature below 10° C
  4. stirringAfter stirring at 0-10° C. for 1.5 hours
  5. customisolate the product
  6. filtrationby filtration
  7. washrinse with cold (0-3° C.) 2:1/Water
  8. customDry the solid in a vacuum oven at 50° C.

Sources & evidence

ORD record
ord-fbb3ae3ac6ca4104bf463ca352c36bf2
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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