Staurosporine → Biphenyl

HRID 438179

Reaction equation

HRID 438179 reaction equation
CN[C@@H]1C[C@H]2O[C@@](C)([C@@H]1OC)n1c3ccccc3c3c4c(c5c6ccccc6n2c5c31)C(=O)NC4.O=Cc1nc2ccccc2s1>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)Cc2nc3ccccc3s2)C[C@H]2O[C@]1(C)n1c3ccccc3c3c4c(c5c6ccccc6n2c5c31)C(=O)NC4

Participants

10

Reactant 2

HCID 44259StaurosporineHCID 2416081,3-Benzothiazole-2-carbaldehyde

Product 4

HCID 7095BiphenylHCID 44259StaurosporineHCID 268122(1,3-Benzothiazol-2-yl)methanolHCID 178496698HCID 178496698, 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-3891bc09a5f544cbb002999a1e653e2a
Source dataset
Cernak miniaturized reductive amination
Original link
View source

Linked notes

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