Diisopropylethylamine → HCID 59743610, compound

HRID 1947055Notes

Reaction equation

HRID 1947055 reaction equation
C(S([C:8]1[N:13]=[C:12]([N:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]([S:23]([NH2:26])(=[O:25])=[O:24])=[CH:15]2)[CH:11]=[CH:10][N:9]=1)(=O)=O)CCC.C([N:29]([CH:33]([CH3:35])[CH3:34])[CH:30](C)C)C>CN1C(=O)CCC1>[CH3:16][S:23]([N:29]([CH3:30])[CH:33]1[CH2:34][CH2:17][CH:22]([NH:14][C:8]2[N:13]=[C:12]([N:14]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[C:16]([S:23]([NH2:26])(=[O:24])=[O:25])=[CH:15]3)[CH:11]=[CH:10][N:9]=2)[CH2:21][CH2:35]1)(=[O:25])=[O:24]

Participants

4

Reactant 2

HCID 81531DiisopropylethylamineHCID 69307199HCID 69307199, compound

Product 1

HCID 59743610HCID 59743610, compoundYield 120.6%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

1-(2-Butylsulfonyl-pyrimidin-4-yl)-1H-indole-3-sulfonic acid amide (250 mg, 0.634 mmol), trans-(N-methyl-N-methylsulfonyl)cyclohexyldiamine acetate (422 mg, 1.584 mmol) and N-ethyl-diisopropylamine (205 mg, 1.584 mmol) were combined in a microwave vial, NMP added under N2, and the vial capped and stirred for 5 min at RT. The vial was then heated to 170° C. in a microwave reactor for 2.5 h, and left to stand at RT overnight. The mixture was then poured into ice water, and the resulting light yellow solid filtered, washed with water (30 mL) and Et2O (40 mL) and air-dried. The crude product was recrystallized from EtOAc-CHCl3 to provide 1-{2-[4-(methanesulfonyl-methyl-amino)-cyclohexylamino]-pyrimdin-4-yl}-1H-indole-3-sulfonic acid amide (183 mg, 60% yield) as a light yellow solid (Compound 321).

Workup

  1. customthe vial capped
  2. temperatureThe vial was then heated to 170° C. in a microwave reactor for 2.5 h
  3. waitleft
  4. waitto stand at RT overnight
  5. filtrationthe resulting light yellow solid filtered
  6. washwashed with water (30 mL) and Et2O (40 mL)
  7. customair-dried
  8. customThe crude product was recrystallized from EtOAc-CHCl3

Sources & evidence

ORD record
ord-0c32080db1204712a2379234d6482b12
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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