Ammonia → HCID 57386411, compound

HRID 1965129Notes

Reaction equation

HRID 1965129 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:11]3([N:15]=[C:14]([CH3:16])[C:13](=S)[NH:12]3)[CH2:10][CH:9]([CH:18]3[CH2:23][CH2:22][O:21][C:20]([CH3:25])([CH3:24])[CH2:19]3)[O:8][C:5]2=[CH:6][CH:7]=1.[NH3:26].CO>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:11]3([N:12]=[C:13]([NH2:26])[C:14]([CH3:16])=[N:15]3)[CH2:10][CH:9]([CH:18]3[CH2:23][CH2:22][O:21][C:20]([CH3:25])([CH3:24])[CH2:19]3)[O:8][C:5]2=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 222Ammonia2×HCID 887MethanolHCID 86667278HCID 86667278, compound

Product 1

HCID 57386411HCID 57386411, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

6-Bromo-2-(2,2-dimethyltetrahydro-2H-pyran-4-yl)-4′-methylspiro[chroman-4,2′-imidazole]-5′(1′H)-thione (Example 49 Step 2), directly from the previous step was dissolved in dry DMF (4 mL) in a microwave vial. Ammonia, 7M in MeOH (18 mL, 126 mmol) was added. The vial was sealed and the reaction was heated at 100° C. for 60 min in a microwave reactor (fixed hold time). The mixture was concentrated and the residue was dissolved in ammonia (7M in MeOH, 18 mL, 126 mmol) and heated at 120° C. for 30 min in a microwave reactor. This cycle was repeated three more times. After evaporation of the solvent, the remaining product was subjected to flash chromatography (0-7% of MeOH(NH3) in DCM) to give the title compound as a mixture of isomers (1.29 g, 30% yield over two steps): MS (ES+) m/z 406 [M+H]+.

Workup

  1. customThe vial was sealed
  2. concentrationThe mixture was concentrated
  3. temperatureheated at 120° C. for 30 min in a microwave reactor
  4. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-69b11f7b0ef54898b85a6f83550f97aa
Source dataset
uspto-grants-2013_04
Patent number
US08415483B2

Reaction notes

Loading…