HCID 54000108, compound → HCID 86602156, compound

HRID 1711983Notes

Reaction equation

HRID 1711983 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[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14][C:13]=2[O:22][S:23]([C:26]([F:29])([F:28])[F:27])(=[O:25])=[O:24])=[N:4][N:3]=1.[NH2:30][C@H:31]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:32]([OH:37])([CH2:35][CH3:36])[CH2:33][CH3:34]>>[CH2:33]([C:32]([OH:37])([CH2:35][CH3:36])[C@H:31]([NH:30][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14][C:13]=2[O:22][S:23]([C:26]([F:29])([F:28])[F:27])(=[O:25])=[O:24])=[N:4][N:3]=1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[CH3:34]

Participants

3

Reactant 2

HCID 54000108HCID 54000108, compoundHCID 58174052HCID 58174052, compound

Product 1

HCID 86602156HCID 86602156, compoundYield 55.3%

Conditions

Temperature
120 °C

Procedure

To trifluoromethanesulfonic acid 1-(4-chlorophthalazin-1-yl)-naphthalen-2-yl ester (600 mg, 1.37 mmol) was added 3-((R)-aminophenyl-methyl)pentan-3-ol (1.06 g, 5.49 mmol). The resulting suspension was stirred for 24 hrs at 120° C. The mixture was purified by flash chromatography on silica gel (toluene/EtOAc 10:0→5:1) followed by crystallization from diethyl ether to give 451 mg of the title compound as a white powder as a mixture of diastereomers. (yield: 55%)

Workup

  1. customThe mixture was purified by flash chromatography on silica gel (toluene/EtOAc 10:0→5:1)
  2. customfollowed by crystallization from diethyl ether

Sources & evidence

ORD record
ord-f710960f9f704641b15a4c8232023374
Source dataset
uspto-grants-2010_09
Patent number
US07790882B2

Reaction notes

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