Water → HCID 117600333, compound

HRID 931664Notes

Reaction equation

HRID 931664 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]2[O:10][C:11]3[C:16]([C@@:17]4([CH2:22][CH2:21][O:20][C:19]([NH2:23])=[N:18]4)[C:4]=2[CH:3]=1)=[CH:15][C:14]([NH2:24])=[CH:13][CH:12]=3.[O:25]1[CH2:30][CH:29]=[C:28](B2OC(C)(C)C(C)(C)O2)[CH2:27][CH2:26]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O>O1CCOCC1.O.C(C1C(C(C)(C)C)=C([Pd]Cl)C=CC=1NC)(C)(C)C>[O:25]1[CH2:26][CH:27]=[C:28]([C:2]2[N:7]=[C:6]([O:8][CH3:9])[C:5]3[O:10][C:11]4[C:16]([C@@:17]5([CH2:22][CH2:21][O:20][C:19]([NH2:23])=[N:18]5)[C:4]=3[CH:3]=2)=[CH:15][C:14]([NH2:24])=[CH:13][CH:12]=4)[CH2:29][CH2:30]1

Participants

7

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 112180533,6-Dihydro-2H-pyran-4-boronic acid pinacol esterHCID 117600786HCID 117600786, compound

Product 1

HCID 117600333HCID 117600333, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 178482226HCID 178482226, compoundCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

A mixture of (S)-3-chloro-1-methoxy-5′,6′-dihydrospiro[chromeno[2,3-c]pyridine-5,4′-[1,3]oxazine]-2′,7-diamine (0.183 g, 0.528 mmol), 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.222 g, 1.055 mmol), 1,1-bis[(di-t-butyl-p-methylaminophenyl]palladium(ii) chloride (0.019 g, 0.026 mmol) and potassium phosphate tribasic (0.336 g, 1.583 mmol) in dioxane/water (21 mL) was heated in microwave at 130° C. for 40 min. The mixture was poured into water and extracted with EtOAc. The combined organics were dried over Na2SO4, filtered, concentrated and chromatographed on silica gel using 0-5% 2M NH3 MeOH/DCM to afford a yellow solid as (S)-3-(3,6-dihydro-2H-pyran-4-yl)-1-methoxy-5′,6′-dihydrospiro[chromeno[2,3-c]pyridine-5,4′-[1,3]oxazine]-2′,7-diamine (0.166 g, 0.421 mmol, 80% yield).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organics were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed on silica gel using 0-5% 2M NH3 MeOH/DCM

Sources & evidence

ORD record
ord-9bb675abd7f545cba935de6ec551db0c
Source dataset
uspto-grants-2016_03
Patent number
US09296759B2

Reaction notes

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