Triethylamine → HCID 59240656, compound

HRID 42198Notes

Reaction equation

[CH2:1]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([N:18]2[CH2:23][CH2:22][N:21]([C:24]3[CH:29]=[N:28][C:27]([C:30]([OH:34])([CH3:33])[CH2:31][OH:32])=[CH:26][N:25]=3)[CH2:20][CH2:19]2)=[N:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[S:42](Cl)([CH3:45])(=[O:44])=[O:43]>C1COCC1>[CH2:1]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([N:18]2[CH2:19][CH2:20][N:21]([C:24]3[CH:29]=[N:28][C:27]([C:30]([OH:34])([CH3:33])[CH2:31][O:32][S:42]([CH3:45])(=[O:44])=[O:43])=[CH:26][N:25]=3)[CH2:22][CH2:23]2)=[N:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2-[4-(4-Benzyl-phthalazin-1-yl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl-5′-yl]-propane-1,2-diol (100 mg, 0.219 mmol) is combined with THF (1.5 mL). The reaction is chilled to 0° C. and triethylamine (95 μL, 0.329 mmol) is added followed by mesyl chloride (100 μL, 0.2 M in THF, 0.263 mmol). The reaction is allowed to warm to room temperature and stir for 96 h. Reaction is quenched with saturated ammonium chloride solution (0.5 mL), diluted with additional water and extracted with EtOAc. Wash combined organics with brine. Concentrate organics in vacuo to afford the title compound (117 mg, 99%).

Workup

temperatureto warm to room temperature
customReaction
customis quenched with saturated ammonium chloride solution (0.5 mL)
additiondiluted with additional water
extractionextracted with EtOAc
washWash

Sources & evidence

ORD record: ord-e9ff13a2e8ca467bb779d805bc0a466d
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536168B2

Reaction notes

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