HCID 22326713, compound → HCID 22326660, compound

HRID 495447Notes

Reaction equation

HRID 495447 reaction equation
I[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH3:12])=[N:9]2)=[C:4]([O:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][CH:19]([CH2:22][C:23]3[CH:24]=[CH:25][C:26]4[O:31][CH2:30][C:29](=[O:32])[NH:28][C:27]=4[CH:33]=3)[CH2:18][CH2:17]2)[CH:3]=1.[Cu][C:35]#[N:36]>>[CH3:12][C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][C:2]([C:35]#[N:36])=[CH:3][C:4]=2[O:13][CH2:14][CH2:15][N:16]2[CH2:17][CH2:18][CH:19]([CH2:22][C:23]3[CH:24]=[CH:25][C:26]4[O:31][CH2:30][C:29](=[O:32])[NH:28][C:27]=4[CH:33]=3)[CH2:20][CH2:21]2)[N:9]=1

Participants

3

Reactant 2

HCID 22326713HCID 22326713, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 22326660HCID 22326660, compoundYield 23.5%

Conditions

Temperature
90 °C

Procedure

A mixture of 6-{1-[2-(7-Iodo-2-methyl-quinolin-5-yloxy)-ethyl]-piperidin-4-ylmethyl}-4H-benzo[1,4]oxazin-3-one (155 mg, 0.28 mmol) and copper (I) cyanide (50 mg, 0.56 mmol) in N-methylpyrrolidinione (2 mL) was stirred at 90° C. for 18 hrs. Upon cooling to room temperature the reaction mixture was partitioned between dichloromethane (5 mL) and ammonia (0.880, 5 mL). The organic layer was separated and applied directly to a 10 g pre-packed silica column eluting with 0-20% methanol in ethyl acetate to afford the title compound as a yellow oil (30 mg, 23%).

Workup

  1. temperatureUpon cooling to room temperature the reaction mixture
  2. customwas partitioned between dichloromethane (5 mL) and ammonia (0.880, 5 mL)
  3. customThe organic layer was separated
  4. washeluting with 0-20% methanol in ethyl acetate

Sources & evidence

ORD record
ord-2f85803f8e6343af996fa16acdb9017c
Source dataset
uspto-grants-2005_09
Patent number
US06939871B2

Reaction notes

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