Water → HCID 15956290, compound

HRID 356606Notes

Reaction equation

HRID 356606 reaction equation
[CH2:1]([N:3]1[C:9]2[N:10]=[CH:11][CH:12]=[CH:13][C:8]=2[C:7](=[O:14])[N:6]([CH3:15])[C:5]2[CH:16]=[CH:17][C:18]([C:20]3[CH:24]=[CH:23][NH:22][CH:21]=3)=[N:19][C:4]1=2)[CH3:2].ClS([N:29]=[C:30]=O)(=O)=O.O>CN(C=O)C.CC#N>[C:30]([C:21]1[NH:22][CH:23]=[CH:24][C:20]=1[C:18]1[CH:17]=[CH:16][C:5]2[N:6]([CH3:15])[C:7](=[O:14])[C:8]3[CH:13]=[CH:12][CH:11]=[N:10][C:9]=3[N:3]([CH2:1][CH3:2])[C:4]=2[N:19]=1)#[N:29].[C:30]([C:23]1[NH:22][CH:21]=[C:20]([C:18]2[CH:17]=[CH:16][C:5]3[N:6]([CH3:15])[C:7](=[O:14])[C:8]4[CH:13]=[CH:12][CH:11]=[N:10][C:9]=4[N:3]([CH2:1][CH3:2])[C:4]=3[N:19]=2)[CH:24]=1)#[N:29]

Participants

7

Reactant 3

HCID 962WaterHCID 70918Chlorosulfonyl isocyanateHCID 463562HCID 463562, compound

Product 2

HCID 15956290HCID 15956290, compoundHCID 15956291HCID 15956291, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 5,11-dihydro-11-ethyl-5-methyl-2-(3-pyrrolyl)-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (0.093 g) in DMF (1 mL) and CH3CN (1 mL) was cooled to -50° C., and chlorosulfonyl isocyanate (0.041 g) was added in one portion. The resulting mixture was allowed to warm to room temperature and stirred for 2 h, then poured into water, extracted with CH2 Cl2, dried (anhyd Na2SO4), filtered, and evaporated. The residue was purified by preparative plate chromatography (ether) to give two pure compounds. Crystallization of each of these pure compounds from ethyl acetate/pet ether provided 0.038 g of the title compound, mp 262°-263° C., and 0.038 g of 2-(2-cyanopyrrol-4-yl)-5,11-dihydro-11-ethyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one, mp 268°-269° C.

Workup

  1. extractionextracted with CH2 Cl2
  2. dry with materialdried (anhyd Na2SO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by preparative plate chromatography (ether)
  6. customto give two pure compounds
  7. customCrystallization of each of these pure compounds from ethyl acetate/pet ether

Sources & evidence

ORD record
ord-eaf6db1c3954429fa029ffbc32044d87
Source dataset
uspto-grants-1998_11
Patent number
US05837704

Reaction notes

Loading…