Tetrahydrofuran → HCID 68700570, compound

HRID 1619222Notes

Reaction equation

HRID 1619222 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][NH:11][CH2:12]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:17]1[N:22]=[CH:21][CH:20]=[CH:19][N:18]=1.C(N(CC)CC)C.C1COCC1>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH:9]2[CH2:15][CH2:14][CH:13]1[CH2:12][N:11]([C:17]1[N:22]=[CH:21][CH:20]=[CH:19][N:18]=1)[CH2:10]2)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 744042-ChloropyrimidineHCID 157409088-Boc-3,8-diaza-bicyclo(3.2.1)octane

Product 1

HCID 68700570HCID 68700570, compoundYield 71.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3,8-diaza-bicyclo[3,2,1]octane-8-carboxyli acid tert-butyl ester (50 mg, 0.24 mmol), 2-chloropyrimidine (27 mg, 0.24 mmol), triethylamine (0.1 ml, 0.72 mmol) and THF (2.5 ml) was heated at 180° C. for 10 minutes. The solution was concentrated to afford a solid residue that was dissolved in dichloromethane, which was washed sequentially with sat. aq. sodium bicarbonate and brine, dried (Na2SO4), filtered, and concentrated to afford 50 mg (71%) of the product as a brown solid: 1H NMR (400 MHz, CDCl3): δ 8.30 (d, J=12.0 Hz, 2H), 6.52 (t, J=12.0 Hz, 1H), 4.38-4.29 (m, 4H), 3.13 (sb, 2H), 2.42 (m, 2H), 1.69 (q, J=18.0 Hz, 2H), 1.49 (s, 9H); MS (M+1)=291.

Workup

  1. concentrationThe solution was concentrated
  2. customto afford a solid residue that
  3. washwhich was washed sequentially with sat. aq. sodium bicarbonate and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c2e268340fab41d79f84456309e7be59
Source dataset
uspto-grants-2014_07
Patent number
US08772291B2

Reaction notes

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