Dimethylformamide → [2-Chloro-4-(3-methyl-pyrazol-1-yl)-phenyl]-(11H-5-oxa-4,10-diaza-dibenzo[a,d]cyclohepten-10-yl)-methanone

HRID 2288683Notes

Reaction equation

HRID 2288683 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9](F)[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[C:12](Cl)(=O)[C:13](Cl)=O.[N:18]1[C:23]2[O:24][C:25]3[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=3[NH:27][CH2:28][C:22]=2[CH:21]=[CH:20][CH:19]=1.[CH2:33]([N:35](CC)CC)[CH3:34].C[N:41](C)C=O>ClCCl>[Cl:1][C:2]1[CH:10]=[C:9]([N:35]2[CH:33]=[CH:34][C:12]([CH3:13])=[N:41]2)[CH:8]=[CH:7][C:3]=1[C:4]([N:27]1[C:26]2[CH:29]=[CH:30][CH:31]=[CH:32][C:25]=2[O:24][C:23]2[N:18]=[CH:19][CH:20]=[CH:21][C:22]=2[CH2:28]1)=[O:6]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 752592-Chloro-4-fluorobenzoic acidHCID 158959295,6-Dihydropyrido[2,3-b][1,5]benzoxazepine

Product 1

HCID 9931754[2-Chloro-4-(3-methyl-pyrazol-1-yl)-phenyl]-(11H-5-oxa-4,10-diaza-dibenzo[a,d]cyclohepten-10-yl)-methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Under anhydrous conditions a mixture of 2-chloro-4-fluorobenzoic acid (0.37 g, 2.12 mmol) and oxalyl chloride (0.303 mL, 2.3 mmol) in 10 mL of dichloromethane containing a catalytic amount of dimethylformamide was stirred at room temperature until gas evolution ceased. The crude acid chloride solution was then added portionwise to a stirred solution of 6H-pyrido[2,3-b][1,5]benzoxazepine of Step A (0.45 g, 2.12 mmol) and triethylamine (0.35 mL, 2.5 mmol) in 15 mL of dichloromethane. The reaction mixture was stirred overnight at ambient temperature, washed with water and dried over sodium sulfate. Evaporation of the solvent provided the crude title compound as a gummy solid which was used as such in the next step. NMR (DMSO-d6, 400 MHz): δ 5.1 (broad, 2H, CH2N), 6.9-7.5 (m, 8H), 7.92 (d, 1H), 8.22 (m, 1H) MS (EI, m/z): 354 [M]+, 319, 198, 157

Workup

  1. stirringThe reaction mixture was stirred overnight at ambient temperature
  2. washwashed with water
  3. dry with materialdried over sodium sulfate
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-4d445014a051422dbff3cfc81809e6cc
Source dataset
uspto-grants-2000_07
Patent number
US06090803

Reaction notes

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