Water → HCID 89123990, compound

HRID 2362395Notes

Reaction equation

HRID 2362395 reaction equation
[NH2:1][C@H:2]([C:13]1C=NC=C(Br)C=1)[C@@H:3]([C:5]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:6]=1F)[OH:4].[Cl:20][C:21]1[N:26]=C[N:24]=[C:23]([C@@H](NC(=O)OC(C)(C)C)[C@@H](C2C=CC=C(F)C=2)O)[CH:22]=1.O.C(O)(C(F)(F)F)=O>CC#N>[ClH:20].[ClH:20].[NH2:1][C@H:2]([C:13]1[N:26]=[C:21]([Cl:20])[CH:22]=[CH:23][N:24]=1)[C@@H:3]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]([F:11])[CH:10]=1)[OH:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 69281835HCID 69281835, compoundHCID 89136642HCID 89136642, compound

Product 1

HCID 89123990HCID 89123990, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Prepared according to the same procedure as (1R,2R)-2-amino-2-(5-bromopyridin-3-yl)-1-(2,5-difluorophenyl)ethanol, starting with tert-butyl (1R,2R)-1-(6-chloropyrimidin-4-yl)-2-(3-fluorophenyl)-2-hydroxyethylcarbamate. Analytical HPLC method: Phenomenex LUNA C18, 50×2 3μ, A=90% H2O/10% CH3CN, B=90% CH3CN/10% H2O, Modifier 0.1% TFA, 0.00 min=0% B, 4.0 min=100% B, 5.0 min=100% B, Flow rate=0.8 mL/min., TR=1.823 min, Mass spec.: 268.1

Workup

  1. customPrepared
  2. custom=1.823 min, Mass spec

Sources & evidence

ORD record
ord-cede6063f2e14db0b4f41ea050e384ca
Source dataset
uspto-grants-2014_04
Patent number
US08691821B2

Reaction notes

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