Acetic Acid → 4-(4-Chlorobenzoyl)-1-[4-(2,5-dihydro-1h-pyrrol-1-ylcarbonyl)benzyl]-6-methoxy-1,3,4,5-tetrahydrobenzo[e][1,4]diazepin-2-on

HRID 2417511Notes

Reaction equation

HRID 2417511 reaction equation
[NH2:1][C:2]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[C:3]=1[CH2:4][N:5]([CH2:15][C:16](OCC)=[O:17])[C:6](=[O:14])[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1.[N:27]1([C:32]([C:34]2[CH:41]=[CH:40][C:37]([CH:38]=O)=[CH:36][CH:35]=2)=[O:33])[CH2:31][CH:30]=[CH:29][CH2:28]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(N(CC)CC)C>ClCCl.[OH-].[Na+].C(O)C.C(OCC)(=O)C>[Cl:13][C:10]1[CH:9]=[CH:8][C:7]([C:6]([N:5]2[CH2:4][C:3]3[C:21]([O:25][CH3:26])=[CH:22][CH:23]=[CH:24][C:2]=3[N:1]([CH2:38][C:37]3[CH:36]=[CH:35][C:34]([C:32]([N:27]4[CH2:31][CH:30]=[CH:29][CH2:28]4)=[O:33])=[CH:41][CH:40]=3)[C:16](=[O:17])[CH2:15]2)=[O:14])=[CH:12][CH:11]=1

Participants

10

Reactant 5

HCID 176Acetic AcidHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 226325974-(2,5-dihydro-1H-pyrrol-1-ylcarbonyl)benz-aldehydeHCID 86589882Ethyl [(2-amino-6-methoxybenzyl)-(4-chlorobenzoyl)amino]acetate

Product 1

HCID 226324534-(4-Chlorobenzoyl)-1-[4-(2,5-dihydro-1h-pyrrol-1-ylcarbonyl)benzyl]-6-methoxy-1,3,4,5-tetrahydrobenzo[e][1,4]diazepin-2-on

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent3×HCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

243 mg (0.65 mmol) of ethyl [(2-amino-6-methoxybenzyl)-(4-chlorobenzoyl)amino]acetate was dissolved in 5 ml of dichloromethane. 156 mg (0.78 mmol) of 4-(2,5-dihydro-1H-pyrrol-1-ylcarbonyl)-benzaldehyde and 0.074 ml (1.3 mmol) of acetic acid were added to the obtained solution, and they were stirred at room temperature for 30 minutes. 340 mg (1.6 mmol) of sodium triacetoxyborohydride was added to the reaction mixture, and they were stirred at room temperature overnight. After the treatment with dichloromethane as the extracting solvent by an ordinary method, the obtained crude product was dissolved in a mixture of 2 ml of 1 N sodium hydroxide and 10 ml of ethanol, and the obtained solution was stirred at room temperature for 5 hours. After the treatment with ethyl acetate as the extracting solvent by an ordinary method, the obtained crude product was dissolved in 5 ml of dichloromethane. 131 mg (0.78 mmol) of 2-chloro-1,3-dimethyl-imidazonium chloride and 0.19 ml (1.3 mmol) of triethylamine were added to the obtained solution, and they were stirred overnight. The solvent was evaporated, and the obtained crude product was treated in the same manner as in step 3 in Example 1 to obtain the title compound.

Workup

  1. stirringwere stirred at room temperature overnight
  2. stirringthe obtained solution was stirred at room temperature for 5 hours
  3. stirringwere stirred overnight
  4. customThe solvent was evaporated
  5. customthe obtained crude product
  6. additionwas treated in the same manner as in step 3 in Example 1

Sources & evidence

ORD record
ord-98c0980a289a4b51b5acf63288ce4e42
Source dataset
uspto-grants-2004_11
Patent number
US06825191B2

Reaction notes

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