Ammonia → HCID 135770543, compound

HRID 2288021Notes

Reaction equation

HRID 2288021 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3=[CH:14][C:15]4[C:16](=[O:33])[NH:17][C:18]([C:22]5[CH:27]=[CH:26][C:25](Br)=[CH:24][C:23]=5[O:29][CH2:30][CH2:31][CH3:32])=[N:19][C:20]=4[CH:21]=[C:12]3[N:11]=[CH:10]2)=[CH:4][CH:3]=1.[Cu][C:35]#[N:36].N>CN1CCCC1=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3=[CH:14][C:15]4[C:16](=[O:33])[NH:17][C:18]([C:22]5[CH:27]=[CH:26][C:25]([C:35]#[N:36])=[CH:24][C:23]=5[O:29][CH2:30][CH2:31][CH3:32])=[N:19][C:20]=4[CH:21]=[C:12]3[N:11]=[CH:10]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 135770615HCID 135770615, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 135770543HCID 135770543, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

1-(4-Fluorophenylmethyl)-6-(4-bromo-2-propoxyphenyl)-1H-imidazo[4,5-g]quinazolin-8(7H)-one (507 mg, 1 mmol) was dissolved in 6 mL N-methyl-2-pyrrolidinone containing copper (I) cyanide (178 mg, 2 mmol). The reaction was heated to reflux overnight, then cooled to room temperature and poured into 100 mL of 2N aqueous ammonia solution. The solid that precipitated was collected by filtration and washed first with 2N aqueous ammonia, then water and dried in a vacuum oven at 45° C. overnight to afford the title compound as a yellow solid (464 mg, 0.91 mmol, 91% yield). HPLC: (YMC S5 ODS 4.6×50 mm column, 4 minute gradient-0% B to 100% B, 4 mL/min flow, solvent A: 10% MeOH-90% H2O-0.2% H3PO4, solvent B: 90% MeOH-10% H2O-0.2% H3PO4) retention time 3.65 minutes.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux overnight
  3. customThe solid that precipitated
  4. filtrationwas collected by filtration
  5. washwashed first with 2N aqueous ammonia
  6. dry with materialwater and dried in a vacuum oven at 45° C. overnight

Sources & evidence

ORD record
ord-23671517f60f4e9ab3550c3fec52f439
Source dataset
uspto-grants-2000_07
Patent number
US06087368

Reaction notes

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