Dimethylformamide → HCID 178521275, compound

HRID 1947009Notes

Reaction equation

HRID 1947009 reaction equation
Br[CH2:2][CH2:3][OH:4].[NH2:5][C:6]1[CH:14]=[C:13]2[C:9]([CH:10]=[N:11][N:12]2[C:15]2[CH:20]=[CH:19][N:18]=[C:17]([NH:21][C@H:22]3[CH2:27][CH2:26][C@H:25]([OH:28])[CH2:24][CH2:23]3)[N:16]=2)=[CH:8][CH:7]=1.C(=O)(O)[O-].[Na+].CN(C=O)C>C(#N)C.CO.CCOCC>[OH:4][CH2:3][CH2:2][NH:5][C:6]1[CH:14]=[C:13]2[C:9]([CH:10]=[N:11][N:12]2[C:15]2[CH:20]=[CH:19][N:18]=[C:17]([NH:21][C@H:22]3[CH2:23][CH2:24][C@H:25]([OH:28])[CH2:26][CH2:27]3)[N:16]=2)=[CH:8][CH:7]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 108982-Bromoethanol2×HCID 516892Sodium BicarbonateHCID 178507323HCID 178507323, compound

Product 1

HCID 178521275HCID 178521275, compoundYield 26.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

2-Bromoethanol (42 μL, 0.6 mmol) was added to a mixture of trans-4-[4-(6-amino-indazol-1-yl)-pyrimidin-2-ylamino]-cyclohexanol (100 mg, 0.30 mmol) and sodium bicarbonate (25 mg, 0.30 mmol) in acetonitrile (1 mL), and the resulting mixture heated to 80° C. for 2 h. DMF (0.5 mL) was added, and the resulting mixture heated to 80° C. overnight. A second aliquot of 2-bromoethanol (20 μL) was added, and heating continued for 3 days. The resulting mixture was diluted with MeOH, and Et2O was added. The gummy residue which crashed out of solution was purified by preparative TLC to give trans-4-{4-[6-(2-hydroxyethylamino)-indazol-1-yl]-pyrimidin-2-ylamino}-cyclohexanol (29 mg) as a yellow solid. MS=369 [M+H]+.

Workup

  1. temperaturethe resulting mixture heated to 80° C. overnight
  2. temperatureheating
  3. additionwas added
  4. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-cf340727d53e45688c1dc98c0c99d673
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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