Water → 4-{4-[4-(3-Sulfamoyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexanecarboxylic acid ethyl ester

HRID 1947046Notes

Reaction equation

HRID 1947046 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH:9]([NH2:12])[CH2:8][CH2:7]1)=[O:5])[CH3:2].CCN(C(C)C)C(C)C.C(S([C:28]1[N:33]=[C:32]([N:34]2[C:42]3[C:37](=[C:38]([O:43][CH2:44][CH2:45][CH2:46][S:47]([NH2:50])(=[O:49])=[O:48])[CH:39]=[CH:40][CH:41]=3)[CH:36]=[CH:35]2)[CH:31]=[CH:30][N:29]=1)=O)CCC.O>CN1C(=O)CCC1>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH:9]([NH:12][C:28]2[N:33]=[C:32]([N:34]3[C:42]4[C:37](=[C:38]([O:43][CH2:44][CH2:45][CH2:46][S:47](=[O:48])(=[O:49])[NH2:50])[CH:39]=[CH:40][CH:41]=4)[CH:36]=[CH:35]3)[CH:31]=[CH:30][N:29]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 409963Ethyl 4-aminocyclohexanecarboxylateHCID 69308577HCID 69308577, compound

Product 1

HCID 597434464-{4-[4-(3-Sulfamoyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexanecarboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

4-Aminocyclohexane carboxylic acid ethyl ester (588.4 mg, 3.44 mmol) was dissolved in NMP (5 mL) and treated with DIEA (0.993 mL, 5.7 mmol) and the reaction mixture allowed to stir at RT for 5 min. 3-[1-(2-Butylsulfinyl-pyrimidin-4-yl)-1H-indol-4-yloxy]-propane-1-sulfonic acid amide (500 mg, 1.14 mmol) was then added, and the reaction mixture heated to 120° C. for 1 h. The reaction was then allowed to cool to RT, water was added, the mixture was sonicated, filtered, and the solid dried in vacuo to yield 4-{4-[4-(3-sulfamoyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexanecarboxylic acid ethyl ester (Compound 318).

Workup

  1. temperaturethe reaction mixture heated to 120° C. for 1 h
  2. temperatureto cool to RT
  3. customthe mixture was sonicated
  4. filtrationfiltered
  5. customthe solid dried in vacuo

Sources & evidence

ORD record
ord-49653b28e6584befa0a49993d4e475b8
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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