1-Pyrrolidineethanol → HCID 59186326, compound

HRID 336412Notes

Reaction equation

HRID 336412 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:31]=[C:12]3[CH:13]=[CH:14][CH:15]=[C:16]([C:17]4[CH:18]=[C:19]([S:23]([NH:26][C:27]([CH3:30])([CH3:29])[CH3:28])(=[O:25])=[O:24])[CH:20]=[CH:21][CH:22]=4)[N:11]3[N:10]=2)=[CH:4][CH:3]=1.[N:32]1([CH2:37][CH2:38][OH:39])[CH2:36][CH2:35][CH2:34][CH2:33]1>C(OCC)(=O)C.[Cu]I>[C:27]([NH:26][S:23]([C:19]1[CH:20]=[CH:21][CH:22]=[C:17]([C:16]2[N:11]3[N:10]=[C:9]([NH:8][C:5]4[CH:6]=[CH:7][C:2]([O:39][CH2:38][CH2:37][N:32]5[CH2:36][CH2:35][CH2:34][CH2:33]5)=[CH:3][CH:4]=4)[N:31]=[C:12]3[CH:13]=[CH:14][CH:15]=2)[CH:18]=1)(=[O:25])=[O:24])([CH3:30])([CH3:29])[CH3:28]

Participants

5

Reactant 2

HCID 762881-PyrrolidineethanolHCID 59186231HCID 59186231, compound

Product 1

HCID 59186326HCID 59186326, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 3-(2-(4-bromophenylamino)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-N-tert-butylbenzenesulfonamide (150 mg, 0.3 mmol) and copper (I) iodide (57 mg, 0.3 mmol) in 2-(pyrrolidin-1-yl)ethanol (2 mL) was heated at 140° C. under a nitrogen atmosphere. After 18 hr, the reaction mixture was cooled to 20° C. and diluted with ethyl acetate (100 mL). The solution was washed with water. The collected organic was dried over anhydrous sodium sulfate, filtered, and concentrated. Purification by preparative thin layer chromatography afforded the desired product (58.5 mg, 36% yield). LCMS (ESI) m/z: 535.3. 1H NMR (400 MHz, DMSO-d6), δ: 9.44 (s, 1H), 8.64 (s, 1H), 8.21-8.19 (d, J=8 Hz, 1H), 8.10-7.99 (d, J=8 Hz, 1H), 7.78 (m, 1H), 7.66-7.57 (m, 5H), 7.24-7.22 (d, J=8 Hz, 1H), 6.90-6.88 (d, J=8 Hz, 2H), 4.15-4.10 (m, 2H), 3.20-3.10 (m, 3H), 2.89-3.05 (m, 3H), 1.83-1.79 (m, 4H), 1.11 (s, 9H).

Workup

  1. washThe solution was washed with water
  2. dry with materialThe collected organic was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by preparative thin layer chromatography

Sources & evidence

ORD record
ord-0c916227e99e4b5c86c3e741671a3152
Source dataset
uspto-grants-2014_11
Patent number
US08889673B2

Reaction notes

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