HCID 710092, compound → HCID 11587985, compound

HRID 1094048Notes

Reaction equation

HRID 1094048 reaction equation
[NH2:1][C:2]1[C:3]([CH2:24][NH2:25])=[C:4]([C:16]2C=C(Cl)C=CC=2Cl)[C:5]2[C:10](=[O:11])[N:9]([CH3:12])[C:8](=[O:13])[N:7]([CH3:14])[C:6]=2[N:15]=1.C[C:27]1[CH:31]=[CH:30][S:29][C:28]=1C=C(C#N)C#N>>[NH2:1][C:2]1[C:3]([CH2:24][NH2:25])=[C:4]([C:16]2[S:29][CH:28]=[CH:27][C:31]=2[CH3:30])[C:5]2[C:10](=[O:11])[N:9]([CH3:12])[C:8](=[O:13])[N:7]([CH3:14])[C:6]=2[N:15]=1

Participants

3

Reactant 2

HCID 710092HCID 710092, compoundHCID 11632315HCID 11632315, compound

Product 1

HCID 11587985HCID 11587985, compoundYield 17.1%

Procedure

The title compound was prepared using the procedures described in the preparation of Compound 8 (Example 7). The only difference was that after the synthesis of 2-(3-methyl-thiophen-2-ylmethylene)-malononitrile, the reaction was carried onto the next step without further work-up or purification, and propanol was used instead of ethanol. Furthermore, after the hydrogenation using BH3.THF, the reaction mixture was concentrated. An ample amount of MeOH was added until there was no more bubbling. The mixture was dried in vacuo, and purified by prep. HPLC. After washing the product with EtOAc, an amount of 82.4 mg (17.1% yield) of the title compound was collected. 1H NMR (400 MHz, d6-DMSO): δ ppm 7.80 (br s, 3H), 7.53 (d, J=4.0 Hz, 1H), 7.36 (br s, 2H), 6.96 (d, J=4.0 Hz, 1H), 3.80 (m, 2H), 3.51 (s, 3H), 3.10 (s, 3H). MS [m+H] calc'd for C15H17N5O2S, 332.0, 333.2. found 332.0, 333.2.

Workup

  1. customThe title compound was prepared
  2. customthe reaction was carried onto the next step without further work-up or purification, and propanol
  3. concentrationthe reaction mixture was concentrated
  4. additionAn ample amount of MeOH was added until there
  5. customno more bubbling
  6. customThe mixture was dried in vacuo
  7. custompurified by prep
  8. washAfter washing the product with EtOAc

Sources & evidence

ORD record
ord-cd938c62af704e7092dfd664ae352c49
Source dataset
uspto-grants-2012_03
Patent number
US08133898B2

Reaction notes

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