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Staurosporine → Biphenyl

HRID 438253
Notes
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Reaction equation

HRID 438253 reaction equation
CN[C@@H]1C[C@H]2O[C@@](C)([C@@H]1OC)n1c3ccccc3c3c4c(c5c6ccccc6n2c5c31)C(=O)NC4.O=C1CCN(c2ccc(F)c(F)c2)CC1>CC(=O)N(C)C.CC(=O)O.CC(=O)O[BH-](OC(C)=O)OC(C)=O.CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Na+].[Ti+4]>CO[C@@H]1[C@H](N(C)C2CCN(c3ccc(F)c(F)c3)CC2)C[C@H]2O[C@]1(C)n1c3ccccc3c3c4c(c5c6ccccc6n2c5c31)C(=O)NC4
ParticipantsConditionsWorkupSources & evidenceReaction notes

Participants

10

Reactant 2

HCID 44259StaurosporineHCID 246938011-(3,4-Difluorophenyl)piperidin-4-one

Product 4

HCID 7095BiphenylHCID 44259StaurosporineHCID 10727303HCID 10727303, compoundHCID 178496665HCID 178496665, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidReagentHCID 11026Titanium isopropoxideReagentHCID 5049666Sodium triacetoxyborohydrideReagentHCID 31374DimethylacetamideSolvent7×

Conditions

Temperature
22 °C

Workup

  1. additionThe next morning, the Mosquito(R) was used to dilute the 100 mM reactions to 50 mM via addition of 1 uL DMSO to each reaction well, followed by dispense mixing.
  2. additionThe reactions were diluted with 3x1 uL DMSO (containing PhPh as an internal standard) using the Mosquito(R). The reactions were mixed after each dispense operation.
  3. aliquotMosquito(R) was used to transfer 1 uL of each quenched reaction from the 1,536-well reaction plate to 384-well analytical plates containing 60 uL DMSO for analysis by UPLC.
  4. additionMosquito(R) was used to transfer 1 uL of each quenched reaction from the 1,536-well reaction plate to 384-well analytical plates containing 60 uL DMSO for analysis by UPLC.

Sources & evidence

ORD record
ord-830bf868736e4dc99734f8b4449c5874
Source dataset
Cernak miniaturized reductive amination
DOI
10.1038/s44160-023-00351-1
Original link
View source

Reaction notes

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On this pageParticipantsConditionsWorkupSources & evidenceReaction notes