Ammonia → HCID 9868764, compound

HRID 1741728Notes

Reaction equation

HRID 1741728 reaction equation
O([C:8]([N:10]([O:40]C(OC1C=CC=CC=1)=O)[CH:11]([CH3:39])[C:12]#[C:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[C:20](=[O:24])[N:19]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]3[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=3)=[CH:28][N:27]=1)[CH2:18][CH2:17]2)=[O:9])C1C=CC=CC=1.[NH3:50]>>[NH2:50][C:8]([N:10]([CH:11]([CH3:39])[C:12]#[C:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[C:20](=[O:24])[N:19]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]3[CH:33]=[CH:34][C:35]([F:38])=[CH:36][CH:37]=3)=[CH:28][N:27]=1)[CH2:18][CH2:17]2)[OH:40])=[O:9]

Participants

3

Reactant 2

HCID 222Ammonia2×HCID 19010533HCID 19010533, compound

Product 1

HCID 9868764HCID 9868764, compound

Conditions

Temperature
-78 °C

Procedure

An NH3 (10 mL) solution of 6-{3-[N,O-bis(phenoxycarbonyl)hydroxylamino]-1-butyn-1-yl}-2-{[5-(4-fluorophenyl)-2-pyridyl]-methyl}-1-oxo-1,2,3,4-tetrahydroisoquinoline (310 mg, 0.47 mmol) in a sealed tube is stirred at ambient temperature for 12 hours. The mixture is then cooled to -78° C. and the reaction vessel carefully opened. The ammonia is allowed to evaporate and the resulting material is partitioned between EtOAc (60 mL) and H2O (10 mL). The aqueous phase is extracted with EtOAc (1×25 mL) and the combined organic phases are washed with saturated NaHCO3 solution (2×50 mL), saturated NaCl solution (2×5 mL), dried over MgSO4 and concentrated in vacuo- The resulting pale yellow solid is chromatographed (silica gel, EtOAc then 10% MeOH/CH2Cl2) to afford 6-[3-(N-aminocarbonyl-N-hydroxyamino)-1-butyn-1-yl]-2-{[5-(4-fluorophenyl)-2-pyridyl]-methyl}-1-oxo-1,2,3,4 -tetrahydroisoquinoline, m.p. 118°-120°C.

Workup

  1. customto evaporate
  2. customthe resulting material is partitioned between EtOAc (60 mL) and H2O (10 mL)
  3. extractionThe aqueous phase is extracted with EtOAc (1×25 mL)
  4. washthe combined organic phases are washed with saturated NaHCO3 solution (2×50 mL), saturated NaCl solution (2×5 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo- The resulting pale yellow solid
  7. customis chromatographed (silica gel, EtOAc

Sources & evidence

ORD record
ord-fe5bbc2056e3488085128c627ea5e0e1
Source dataset
uspto-grants-1994_08
Patent number
US05334600

Reaction notes

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