Water → HCID 178481745, compound

HRID 1946991Notes

Reaction equation

HRID 1946991 reaction equation
Cl[N:2]1[C:6](=O)[CH2:5][CH2:4][C:3]1=[O:8].[CH3:9][N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([C:19]2[CH:24]=[CH:23][N:22]=[C:21](SC)[N:20]=2)=[N:11]1.O.CN1C(=O)C[CH2:31][CH2:30]1>>[CH3:9][N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([C:19]2[CH:24]=[CH:23][N:22]=[C:21]([NH:2][C@H:6]3[CH2:31][CH2:30][C@H:3]([OH:8])[CH2:4][CH2:5]3)[N:20]=2)=[N:11]1

Participants

5

Reactant 4

HCID 962WaterHCID 13387N-methyl-2-pyrrolidoneHCID 31398ChlorosuccinimideHCID 597434781-methyl-3-(2-methylsulfanylpyrimidin-4-yl)-1H-indazole

Product 1

HCID 178481745HCID 178481745, compound

Procedure

N-Chlorosuccinimide (239 mg, 1.77 mmol) was added to a solution of 1-methyl-3-(2-methylsulfanyl-pyrimidin-4-yl)-1H-indazole (413 mg, 1.6 mmol) in NMP, and the resulting mixture was stirred at 85° C. for 15 min. trans-Aminocyclohexanol was then added, the reaction mixture stirred for 1 h, then poured into water and extracted twice with EtOAc. The combined organic extracts were dried over Na2SO4, filtered, and evaporated under reduced pressure. The crude residue was purified by preparative TLC to give trans-4-[4-(1-methyl-1H-indazol-3-yl)-pyrimidin-2-ylamino]-cyclohexanol. MS=324 [M+H]+; MP=180-183.3° C. (Compound 77).

Workup

  1. additionwas then added
  2. extractionextracted twice with EtOAc
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe crude residue was purified by preparative TLC

Sources & evidence

ORD record
ord-2ab965ae6e8f41bfb785424fafbb89ae
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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