1,2-Dichloroethane → HCID 118236111, compound

HRID 1481285Notes

Reaction equation

HRID 1481285 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:13]1[CH:18]=[C:17]([C:19]2[CH:27]=[CH:26][C:25]([NH:28][C:29]([O:31][CH3:32])=[O:30])=[CH:24][C:20]=2[C:21]([OH:23])=O)[CH:16]=[CH:15][N:14]=1)[CH2:10][CH:11]=[CH2:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:33]([NH2:36])[CH:34]=[CH2:35].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.CCOC(C)=O>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:13]1[CH:18]=[C:17]([C:19]2[CH:27]=[CH:26][C:25]([NH:28][C:29](=[O:30])[O:31][CH3:32])=[CH:24][C:20]=2[C:21](=[O:23])[NH:36][CH2:33][CH:34]=[CH2:35])[CH:16]=[CH:15][N:14]=1)[CH2:10][CH:11]=[CH2:12])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 7853AllylamineHCID 757711-HydroxybenzotriazoleHCID 90313147HCID 90313147, compound

Product 1

HCID 118236111HCID 118236111, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 24D (0.06 g, 0.136 mmol), prop-2-en-1-amine (9.31 mg, 0.163 mmol), EDC (0.052 g, 0.272 mmol) and HOBT (0.042 g, 0.272 mmol) in DMF (1 mL) was added TEA (0.057 mL, 0.408 mmol). The reaction was stirred at rt for 18 h. The reaction was diluted with EtOAc, washed with water, brine, dried over Na2SO4, filtered, and concentrated. Purification by normal phase chromatography provided 24E (0.056 g, 86%) as a white solid. MS (ESI) m/z: 481.3 (M+H)+.

Workup

  1. washwashed with water, brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by normal phase chromatography

Sources & evidence

ORD record
ord-b3136194a6db48318f498c23c7f61eb4
Source dataset
uspto-grants-2016_08
Patent number
US09409908B2

Reaction notes

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