Diisopropylcarbodiimide → HCID 178521912, compound

HRID 1406435Notes

Reaction equation

HRID 1406435 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[NH2:17])[C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:6].[Cl:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[C:20]=1[N:26]=[C:27]=S.CC(C)N=C=NC(C)C>C1COCC1>[C:8]1([NH:7][C:5]([C:4]2[CH:14]=[CH:15][C:16]3[NH:17][C:27]([NH:26][C:20]4[C:19]([Cl:18])=[CH:24][CH:23]=[CH:22][C:21]=4[Cl:25])=[N:1][C:2]=3[CH:3]=2)=[O:6])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 1232391,3-Dichloro-2-isothiocyanatobenzeneHCID 181854863,4-Diamino-N-phenylbenzamide

Product 1

HCID 178521912HCID 178521912, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of the product obtained at (1b) (250 mg, 0.99 mmol) in 5.0 mL of THF was combined with 1,3-dichloro-2-isothiocyanato-benzene (222 mg, 1.09 mmol) and stirred for 5 h at ambient temperature under nitrogen. DIC (166 μL, 1.04 mmol) was added and the stirred mixture was heated to 55° C. for 16 h. The mixture was filtrated and concentrated i.vac., the residue purified by HPLC (Symmetry C18, 7 μM, eluent gradient: (H2O+0.15% HCOOH)/acetonitrile=95:5->5:95).

Workup

  1. additionA mixture of the product
  2. temperaturethe stirred mixture was heated to 55° C. for 16 h
  3. filtrationThe mixture was filtrated
  4. concentrationconcentrated i.vac
  5. custom, the residue purified by HPLC (Symmetry C18, 7 μM, eluent gradient: (H2O+0.15% HCOOH)/acetonitrile=95:5->5:95)

Sources & evidence

ORD record
ord-23667d384d4942eeacd6f993c24f07e5
Source dataset
uspto-grants-2014_12
Patent number
US08916599B2

Reaction notes

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