3-Methoxyaniline → HCID 59851677, compound

HRID 545064Notes

Reaction equation

HRID 545064 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[CH2:11][C:10](=[O:12])[NH:9][C:8]3[CH:13]=[C:14](I)[CH:15]=[CH:16][C:7]=3[C:6]=2[N:18]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH3:27][O:28][C:29]1[CH:30]=[C:31]([CH:33]=[CH:34][CH:35]=1)[NH2:32]>CN1CCCC1=O>[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[CH2:11][C:10](=[O:12])[NH:9][C:8]3[CH:13]=[C:14]([NH:32][C:31]4[CH:33]=[CH:34][CH:35]=[C:29]([O:28][CH3:27])[CH:30]=4)[CH:15]=[CH:16][C:7]=3[C:6]=2[N:18]=1

Participants

5

Reactant 3

HCID 108243-MethoxyanilineHCID 62657Potassium Phosphate, TribasicHCID 59851934HCID 59851934, compound

Product 1

HCID 59851677HCID 59851677, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
90 °C

Procedure

2-Amino-9-iodo-5H,7H-benzo[b]pyrimido[4,5-d]azepin-6-one (200 mg, 0.568 mmol, 1.0 equiv), anhydrous K3PO4 powder (241 mg, 1.14 mmol, 2.0 equiv) and palladium bis-tri-t-butyl phosphine (58 mg, 0.1136 mmol, 20 mol %) were combined in a sealable vial with a magnetic stir bar under a nitrogen atmosphere (glove box). 3-Methoxyaniline (209 mg, 1.70 mmol, 3.0 equiv) was added, followed by 6 mL of anhydrous N-methylpyrrolidinone. The vial was sealed with a silicone lined crimp cap and removed from the glove box. The vial was sonicated for 2 minutes and then heated to 90° C. (oil bath temperature) for 18 hours. The dark brown solution was diluted with 50 mL of water and the brown solids were collected by filtration and washed with water and then diethyl ether. Purification by silica gel chromatography (10% methanol, 85% dichloromethane, 5% formic acid) afforded an orange powder, which was recrystallized from methanol and diethyl ether to yield 120 mg (61%) of 2-amino-9-(3-methoxy-phenylamino)-5H,7H-benzo[b]pyrimido[4,5-d]azepin-6-one (I-225) as a yellow-orange powder.

Workup

  1. customcrimp cap
  2. customremoved from the glove box
  3. customThe vial was sonicated for 2 minutes
  4. additionThe dark brown solution was diluted with 50 mL of water
  5. filtrationthe brown solids were collected by filtration
  6. washwashed with water
  7. customPurification by silica gel chromatography (10% methanol, 85% dichloromethane, 5% formic acid)
  8. customafforded an orange powder, which
  9. customwas recrystallized from methanol and diethyl ether

Sources & evidence

ORD record
ord-8f8d7d9554294c809d603338dd397c1f
Source dataset
uspto-grants-2011_05
Patent number
US07935694B2

Reaction notes

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