Acetic Acid → HCID 66798095, compound

HRID 1397609Notes

Reaction equation

HRID 1397609 reaction equation
[C@@H:1]1([NH:10][C:11]2[CH:16]=[C:15]([CH2:17][C@H:18]3[CH2:34][C@@H:21]4[O:22]C(C5C=CC(OC)=CC=5)[O:24][CH2:25][C@@H:20]4[CH2:19]3)[N:14]=[CH:13][N:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.O.CC(O)=O>C1COCC1>[C@@H:1]1([NH:10][C:11]2[N:12]=[CH:13][N:14]=[C:15]([CH2:17][C@H:18]3[CH2:34][C@H:21]([OH:22])[C@H:20]([CH2:25][OH:24])[CH2:19]3)[CH:16]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 66798132HCID 66798132, compound

Product 1

HCID 66798095HCID 66798095, compoundYield 91.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-[(1S)-2,3-Dihydro-1H-inden-1-yl]-6-{[(4aS,6S,7aS)-2-(4-methoxyphenyl)-hexahydrocyclopenta[d][1,3]dioxin-6-yl]methyl}pyrimidin-4-amine (0.280 g, 0.61 mmol) was dissolved in THF (2 mL), water (2 mL) and AcOH (6 mL, 0.106 mmol) were added. The mixture was stirred under an atmosphere of argon for 60 h. The mixture was concentrated under reduced pressure and the residue was purified via silica gel chromatography eluting with a gradient of 0 to 10% MeOH in DCM to afford the title compound (0.190 g, 91%). LC/MS: Rt=1.29 min, ES+ 340 (AA standard).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was purified via silica gel chromatography
  3. washeluting with a gradient of 0 to 10% MeOH in DCM

Sources & evidence

ORD record
ord-eb8e4a8853c1491ca1cc256d107da289
Source dataset
uspto-grants-2014_12
Patent number
US08901136B2

Reaction notes

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