HCID 59713612, compound → HCID 10312102, compound

HRID 2223080Notes

Reaction equation

HRID 2223080 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[O:13])[CH:9]([N:14]=[C:15]=[S:16])[N:8]=[C:7]([C:17]3[CH:21]=[CH:20][S:19][CH:18]=3)[C:6]=2[CH:22]=1.[N:23]1([C:29]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:32]([NH2:39])=[CH:31][CH:30]=2)[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1>CC(N(C)C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[O:13])[CH:9]([NH:14][C:15]([NH:39][C:32]3[C:33]4[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=4)[C:29]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)=[CH:30][CH:31]=3)=[S:16])[N:8]=[C:7]([C:17]3[CH:21]=[CH:20][S:19][CH:18]=3)[C:6]=2[CH:22]=1

Participants

4

Reactant 2

HCID 59713612HCID 59713612, compoundHCID 59713770HCID 59713770, compound

Product 1

HCID 10312102HCID 10312102, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
70 °C

Procedure

This reaction was carried out in a multiwell plate. As illustrated in the scheme above, aA mixture of 7-chloro-1,3-dihydro-3-isothiocyanato-1-methyl-5-(3-thienyl)-2H-1,4-benzodiazepin-2-one (156 μL of a 0.128 M solution in (CH2Cl)2, 0.020 mmol), 4-(4-morpholinyl)-1-naphthalenamine (44 μL of a 0.5 M solution in DMA, 0.022 mmol), and (CH2Cl)2 (300 μL) was agitated and heated at 70° C. for 22 h. The reaction was cooled and concentrated in vacuo, and the residue was redissolved in DMA (25 μL) and (CH2Cl)2 (275 μL). Polyamine resin HL (NovaBiochem) was added (20 mg of 4.53 mmol/g, 0.091 mmol), and the mixture was agitated at room temperature overnight. The resin was removed by filtration and washed with additional (CH2Cl)2 and MeOH. The filtrate was concentrated in vacuo to provide the title compound. MS (ESI) (M+H)+=576.

Workup

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated in vacuo
  3. dissolutionthe residue was redissolved in DMA (25 μL)
  4. additionPolyamine resin HL (NovaBiochem) was added (20 mg of 4.53 mmol/g, 0.091 mmol)
  5. stirringthe mixture was agitated at room temperature overnight
  6. customThe resin was removed by filtration
  7. washwashed with additional (CH2Cl)2 and MeOH
  8. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-66c615f5ea2648a8b725a41470633117
Source dataset
uspto-grants-2008_05
Patent number
US07375101B2

Reaction notes

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