Triethylamine → HCID 18381660, compound

HRID 2268911Notes

Reaction equation

HRID 2268911 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:27])[C:7]=1[CH2:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[CH:12]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[NH:11][N:10]=1.C(N(CC)CC)C.[CH3:35][S:36](Cl)(=[O:38])=[O:37].N12CCCN=C1CCCCC2>C(Cl)Cl.O>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:27])[C:7]=1[CH2:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[CH:12]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:11]([S:36]([CH3:35])(=[O:38])=[O:37])[N:10]=1

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 31297Methanesulfonyl chloride3×HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 18381610HCID 18381610, compound

Product 1

HCID 18381660HCID 18381660, compoundYield 110.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

4-(3,5-Dichloro-pyridin-4-ylmethyl)-7-methoxy-1-phenyl-1,2-dihydro-phthalazine (0.16 g, 0.4 mmole), prepared as described in example 111, in dry CH2Cl2 (10 ml), under N2, was added with triethylamine (0.1 ml, 0.72 mmole) and methanesulphonyl chloride (0.037 ml, 0.48 mmole). The mixture was stirred at room temperature overnight, then added again with triethylamine (0.05 ml, 0.36 mmole) and methanesulphonyl chloride (0.02 ml, 0.24 mmole). After 4 hours methanesulphonyl chloride (0.04 ml, 0.48 mmole) and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.085 ml, 0.56 mmole) were added. After 24 hours the mixture was poured into water and the aqueous phase separated and extracted with CH2Cl2. The organic phase was washed in diluted citric acid, anhydrified and dried to give a solid which was flash chromatographed (eluent: petrolatum/ethyl acetate 7:3). The resultant solid was triturated in ethyl ether to give 0.21 g of the title compound (quantitative yield). m.p.: 222.6-224.4° C.

Workup

  1. customthe aqueous phase separated
  2. extractionextracted with CH2Cl2
  3. washThe organic phase was washed in diluted citric acid
  4. customdried
  5. customto give a solid which
  6. customchromatographed (eluent: petrolatum/ethyl acetate 7:3)
  7. customThe resultant solid was triturated in ethyl ether

Sources & evidence

ORD record
ord-e433bde762a745c289da5a76dbf6ad74
Source dataset
uspto-grants-2001_12
Patent number
US06329370B1

Reaction notes

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