Diisopropylethylamine → HCID 66798195, compound

HRID 1747634Notes

Reaction equation

HRID 1747634 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]([CH3:21])[C@H:9]2[C@@H:13]3[O:14][C:15]([CH3:18])([CH3:17])[O:16][C@@H:12]3[C@@H:11]([CH2:19][OH:20])[CH2:10]2)[CH:3]=1.C(N(CC)C(C)C)(C)C.[NH2:31][C@@H:32]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH2:34][CH2:33]1>C(O)CCC>[C@@H:32]1([NH:31][C:2]2[N:7]=[CH:6][N:5]=[C:4]([N:8]([CH3:21])[C@H:9]3[C@@H:13]4[O:14][C:15]([CH3:18])([CH3:17])[O:16][C@@H:12]4[C@@H:11]([CH2:19][OH:20])[CH2:10]3)[CH:3]=2)[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH2:34][CH2:33]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 70000841-Aminoindane, (S)-HCID 86618724HCID 86618724, compound

Product 1

HCID 66798195HCID 66798195, compoundYield 24.1%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
200 °C

Procedure

{(3aR,4R,6R,6aS)-6-[(6-chloropyrimidin-4-yl)(methyl)amino]-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl}methanol (130 mg, 0.41 mmol) was weighed into a microwave reaction tube and dissolved in 1-butanol (1.50 mL). To this solution was added N,N-diisopropylethylamine (0.22 mL, 1.24 mmol) and (S)-(+)-1-aminoindan (0.16 mL, 1.24 mmol) and the mixture was heated in a sealed tube under microwave irradiation at 200° C. for 4 h. The reaction mixture was concentrated under vacuum, and the residue was purified via silica gel column chromatography eluting with a gradient of 2 to 5% methanol in DCM to afford the title compound (40.5 mg, 24%) as a colorless oil. LC/MS: Rt=1.49 min, ES+ 411.5 (AA standard).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customthe residue was purified via silica gel column chromatography
  3. washeluting with a gradient of 2 to 5% methanol in DCM

Sources & evidence

ORD record
ord-a3ced2b243e24e36afca3218220bb6f2
Source dataset
uspto-grants-2015_10
Patent number
US09150525B2

Reaction notes

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