Diisopropylethylamine → HCID 58379032, compound

HRID 1951158Notes

Reaction equation

HRID 1951158 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[N:4][N:3]=1.[NH:19]1[CH2:24][CH2:23][NH:22][CH2:21][C@@H:20]1[CH2:25][OH:26].C(N(C(C)C)CC)(C)C>CS(C)=O>[F:18][C:15]1[CH:16]=[CH:17][C:12]([C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:2]([N:22]3[CH2:23][CH2:24][NH:19][C@@H:20]([CH2:25][OH:26])[CH2:21]3)=[N:3][N:4]=2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 21152391-Chloro-4-(4-fluorophenyl)phthalazineHCID 14288867HCID 14288867, compound

Product 1

HCID 58379032HCID 58379032, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Dissolve 1-chloro-4-(4-fluorophenyl)phthalazine (0.1 g, 0.39 mmol), (R)-piperazin-2-ylmethanol (0.07 g, 0.58 mmol) and diisopropylethylamine (0.34 mL, 1.93 mmol) in DMSO (1 mL). Stir the reaction at 120° C. for 64 h. Purify the reaction mixture by flash silica gel chromatography (0-10% 2 M ammonia/MeOH in CH2Cl2) to yield the title compound as a brown solid (0.11 g, 84%). ES/MS m/z 339.0 (M+1).

Workup

  1. customthe reaction at 120° C. for 64 h
  2. customPurify the reaction mixture by flash silica gel chromatography (0-10% 2 M ammonia/MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-dff56a73642a43d09ee0f2be3fd15005
Source dataset
uspto-grants-2013_03
Patent number
US08404687B2

Reaction notes

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