Cesium carbonate → tert-Butyl 3-{3-[(cyclopentyl{4-[(4-methyl-1-oxophthalazin-2(1H)-yl)methyl]phenyl}acetyl)-amino]-2-methylphenyl}propanoate

HRID 877255Notes

Reaction equation

HRID 877255 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH:29]2[CH2:33][CH2:32][CH2:31][CH2:30]2)[C:10]([NH:12][C:13]2[C:14]([CH3:28])=[C:15]([CH2:19][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH:16]=[CH:17][CH:18]=2)=[O:11])=[CH:5][CH:4]=1.[CH3:34][C:35]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[C:38](=[O:45])[NH:37][N:36]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH:29]1([CH:9]([C:6]2[CH:7]=[CH:8][C:3]([CH2:2][N:37]3[N:36]=[C:35]([CH3:34])[C:44]4[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=4)[C:38]3=[O:45])=[CH:4][CH:5]=2)[C:10]([NH:12][C:13]2[C:14]([CH3:28])=[C:15]([CH2:19][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH:16]=[CH:17][CH:18]=2)=[O:11])[CH2:30][CH2:31][CH2:32][CH2:33]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 211031-Hydroxy-4-methylphthalazineHCID 58136306Tert-butyl 3-[3-({[4-(bromomethyl)phenyl](cyclopentyl)acetyl}amino)-2-methylphenyl]propanoate

Product 1

HCID 58136381tert-Butyl 3-{3-[(cyclopentyl{4-[(4-methyl-1-oxophthalazin-2(1H)-yl)methyl]phenyl}acetyl)-amino]-2-methylphenyl}propanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

50 mg (0.097 mmol) of tert-butyl 3-[3-({[4-(bromomethyl)phenyl](cyclopentyl)acetyl}amino)-2-methylphenyl]propanoate, 19 mg (0.12 mmol) of 4-methylphthalazin-1(2H)-one and 47 mg (0.15 mmol) of cesium carbonate were stirred in 5 ml of DMF at 60° C. for 12 h. After cooling, the reaction mixture was purified directly by preparative HPLC. This gave 43 mg (0.07 mmol, 74% of theory) of the racemic title compound.

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture was purified directly by preparative HPLC

Sources & evidence

ORD record
ord-977b381b6ae64fe4a1926f80faffa428
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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