Triethylamine → HCID 9931699, compound

HRID 1978196Notes

Reaction equation

HRID 1978196 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([C:11]2[CH:15]=[CH:14][N:13]([CH3:16])[N:12]=2)[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.C(N(CC)CC)C.ClC1C=C(Cl)C=C(Cl)C=1C(Cl)=O.[N:36]1[C:41]2[NH:42][C:43]3[CH:50]=[CH:49][CH:48]=[CH:47][C:44]=3[NH:45][CH2:46][C:40]=2[CH:39]=[CH:38][CH:37]=1>ClCCl.CN(C)C1C=CN=CC=1>[Cl:1][C:2]1[CH:10]=[C:9]([C:11]2[CH:15]=[CH:14][N:13]([CH3:16])[N:12]=2)[CH:8]=[CH:7][C:3]=1[C:4]([N:45]1[C:44]2[CH:47]=[CH:48][CH:49]=[CH:50][C:43]=2[NH:42][C:41]2[N:36]=[CH:37][CH:38]=[CH:39][C:40]=2[CH2:46]1)=[O:6]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 27337032,4,6-Trichlorobenzoyl chlorideHCID 10889933HCID 10889933, compoundHCID 110307606,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine

Product 1

HCID 9931699HCID 9931699, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Under anhydrous conditions a solution of 2-chloro-4-(1-methyl-1H-pyrazol-3-yl)-benzoic acid of Step E (2.1 g, 8.88 mmol) and triethylamine (1.3 mL, 9.2 mmol) in 75 mL of dichloromethane was treated in one portion with 2,4,6-trichlorobenzoyl chloride (1.48 mL, 9.2 mmol) and stirred at ambient temperature for 2 hours. To the solution was added the 6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine of Example 1, Step B (1.74 g, 8.9 mmol) followed by 4-dimethylaminopyridine (1.1 g, 8.9 mmol) and stirring was continued for 18 hours. The reaction mixture was washed sequentially with saturated sodium bicarbonate and brine. After drying over sodium sulfate, the solution was concentrated to small volume and absorbed onto silica Merck-60. Elution with ethyl acetate-hexane (gradient from 4:3 to 2:1) gave the pure title compound as a syrup which crystallized from diethylether. The white solid (0.78 g) melted at 196-197° C.

Workup

  1. stirringstirring
  2. waitwas continued for 18 hours
  3. washThe reaction mixture was washed sequentially with saturated sodium bicarbonate and brine
  4. dry with materialAfter drying over sodium sulfate
  5. concentrationthe solution was concentrated to small volume
  6. customabsorbed onto silica Merck-60
  7. washElution with ethyl acetate-hexane (gradient from 4:3 to 2:1)

Sources & evidence

ORD record
ord-adbca378f8b048f1af13d18292d9886a
Source dataset
uspto-grants-2001_05
Patent number
US06235900B1

Reaction notes

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