N-(4-aminocyclohexyl)methanesulfonamide → HCID 59743586, compound

HRID 1947030Notes

Reaction equation

HRID 1947030 reaction equation
[F:1][C:2]([F:27])([F:26])[CH2:3][CH:4]([OH:25])[CH2:5][O:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH:9]=[CH:10][N:11]2[C:16]1[CH:21]=[CH:20][N:19]=[C:18](S(C)=O)[N:17]=1.[NH2:28][CH:29]1[CH2:34][CH2:33][CH:32]([NH:35][S:36]([CH3:39])(=[O:38])=[O:37])[CH2:31][CH2:30]1>CN1C(=O)CCC1>[F:26][C:2]([F:1])([F:27])[CH2:3][CH:4]([OH:25])[CH2:5][O:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH:9]=[CH:10][N:11]2[C:16]1[CH:21]=[CH:20][N:19]=[C:18]([NH:28][CH:29]2[CH2:34][CH2:33][CH:32]([NH:35][S:36]([CH3:39])(=[O:38])=[O:37])[CH2:31][CH2:30]2)[N:17]=1

Participants

4

Reactant 2

HCID 18348422N-(4-aminocyclohexyl)methanesulfonamideHCID 69309652HCID 69309652, compound

Product 1

HCID 59743586HCID 59743586, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

4,4,4-Trifluoro-1-[1-(2-methylsulfinyl-pyrimidin-4-yl)-1H-indol-4-yloxy]-butan-2-ol (0.3 g), N-(4-aminocyclohexyl)-methanesulfonamide (0.514 g) and TEA (0.523 mL) were stirred in NMP (3 mL) at 110° C. for 3 h. After cooling, the resulting solid was filtered washed with H2O and dried. The product was purified on a column using 70% EtOH/hexane to 100% EtOAc, the fractions collected, concentrated in vacuo at 50° C. overnight to yield N-(4-{4-[4-(4,4,4-trifluoro-2-hydroxy-butoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexyl)-methanesulfonamide (Compound 314, 0.227 g).

Workup

  1. temperatureAfter cooling
  2. filtrationthe resulting solid was filtered
  3. washwashed with H2O
  4. customdried
  5. customThe product was purified on a column
  6. customthe fractions collected
  7. concentrationconcentrated in vacuo at 50° C. overnight

Sources & evidence

ORD record
ord-4844e787813d4e998a9a73cacfa8d0ba
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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