1,2-Dichloroethane → 2-[(R)-2-(7-cyclopentylamino-1H-indol-2-yl)-4,5-dihydro-thiazol-4-yl]-N-ethyl-acetamide

HRID 1876332Notes

Reaction equation

HRID 1876332 reaction equation
[CH:1]1([NH:6][C:7]2[CH:8]=[CH:9][CH:10]=[C:11]3[C:15]=2[NH:14][C:13]([C:16]2[S:17][CH2:18][C@@H:19]([CH2:21][C:22]([OH:24])=O)[N:20]=2)=[CH:12]3)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[CH2:26]([NH2:28])[CH3:27].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH:1]1([NH:6][C:7]2[CH:8]=[CH:9][CH:10]=[C:11]3[C:15]=2[NH:14][C:13]([C:16]2[S:17][CH2:18][C@@H:19]([CH2:21][C:22]([NH:28][CH2:26][CH3:27])=[O:24])[N:20]=2)=[CH:12]3)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

8

Reactant 6

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 11198Ethylamine hydrochlorideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 25197052[(R)-2-(7-cyclopentylamino-1H-indol-2-yl)-4,5-dihydro-thiazol-4-yl]acetic acid

Product 1

HCID 595430782-[(R)-2-(7-cyclopentylamino-1H-indol-2-yl)-4,5-dihydro-thiazol-4-yl]-N-ethyl-acetamideYield 41%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound (9 mg, 0.03 mmol) prepared in Example 42 was dissolved in N,N-dimethylformamide (1 ml). Ethylamine hydrochloride (3 mg, 0.03 mmol), EDC (8 mg, 0.04 mmol), HOBT (5 mg, 0.04 mmol) and triethylamine (8 mg, 0.08 mmol) were added thereto, and the mixture was stirred for 8 h at room temperature. After completion of the reaction, saturated sodium bicarbonate solution was added. The mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and filtered. The filtrate was distilled under reduced pressure, and concentrated. The residue was purified by column chromatography to give the title compound (4 mg, Yield 41%).

Workup

  1. additionwas added
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. distillationThe filtrate was distilled under reduced pressure
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-59f9d7186faa4085a44a08f023f73a18
Source dataset
uspto-grants-2012_11
Patent number
US08309586B2

Reaction notes

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