Ethyl Bromide → HCID 68644658, compound

HRID 1159008Notes

Reaction equation

HRID 1159008 reaction equation
[Cl:1][C:2]1[CH:36]=[CH:35][C:5]([CH2:6][NH:7][C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[NH:13][N:12]([C@H:17]([CH3:34])[C@:18]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:27]=2[F:33])([OH:25])[CH2:19][N:20]2[CH:24]=[N:23][CH:22]=[N:21]2)[CH2:11]3)=[CH:4][CH:3]=1.[CH:37](N(C(C)C)CC)(C)[CH3:38].BrCC>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:36]=[CH:35][C:5]([CH2:6][N:7]([CH2:37][CH3:38])[C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[NH:13][N:12]([C@H:17]([CH3:34])[C@:18]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:27]=2[F:33])([OH:25])[CH2:19][N:20]2[CH:24]=[N:23][CH:22]=[N:21]2)[CH2:11]3)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6332Ethyl BromideHCID 81531DiisopropylethylamineHCID 68644829HCID 68644829, compound

Product 1

HCID 68644658HCID 68644658, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2R,3R)-3-(5-(4-chlorobenzylamino)-1H-indazol-2-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol (0.043 g, 0.08 mmol), prepared in Example 244, in N,N′-dimethylformamide (0.5 ml) was added diisopropylethylamine (0.015 ml, 0.08 mmol), followed by stirring for 30 min. The reaction solution was further stirred at 80° C. for 18 hours after the addition of bromoethane (0.019 ml, 0.17 mmol) thereto. The reaction product was diluted with ethyl acetate (10 ml) and washed with saturated ammonium chloride solution (10 ml), and then with brine (10 ml). The organic layer was dried over anhydrous magnesium sulfate and concentrated using vacuum evaporation. The crude product was purified by chromatography on silica gel to give the title compound.

Workup

  1. stirringThe reaction solution was further stirred at 80° C. for 18 hours
  2. washwashed with saturated ammonium chloride solution (10 ml)
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customvacuum evaporation
  6. customThe crude product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-167acd6fbe664322b2d105bbed031052
Source dataset
uspto-grants-2010_10
Patent number
US07812045B2

Reaction notes

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