Pyridine → HCID 86623132, compound

HRID 2262452Notes

Reaction equation

HRID 2262452 reaction equation
[C:1]([NH2:8])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:9]([O:12]C(=O)C)(=[O:11])[CH3:10].N1C=CC=CC=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]([NH2:8])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:9]([O-:12])(=[O:11])[CH3:10]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 77922tert-Butyl carbamate

Product 1

HCID 86623132HCID 86623132, compoundYield 585.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of the Boc-amine (3, 540 mg, 0.451 mmol) in DCM (250 mL) is added acetic anhydride (0.100 mL, 0.979 mmol), pyridine (1.0 mL, 12.4 mmol) and DMAP (20 mg, 0.169 mmol). The reaction is stirred for 3 h, concentrated directly onto SiO2 and chromatographed (gradient elution: 50-70% EtOAc/hexanes) which provides 465 mg of Boc-amine-acetate (4). 1H NMR (400 MHz, d6-DMSO) δ 10.38 (br s, 1H), 9.20 (br d, 1H), 8.79 (br d, 1H), 8.61 (br d, 1H), 8.56 (s, 1H), 8.44-8.41 (m, 1H), 8.38 (d, 1H), 8.24 (s, 1H), 8.11 (d, 1H), 7.48 (br s, 1H), 7.42 (s, 2H), 7.35-7.29 (m, 6H), 6.14 (s, 1H), 5.47 (t, 1H), 5.31-5.26 (m, 1H), 5.19 (dd, 1H), 4.97 (s, 3H), 4.26 (dd, 1H), 3.72 (dd, 1H), 3.38 (s, 3H), 2.70-2.65 (m, 1H), 2.59 (s, 3H), 2.45 (d, 3H), 2.22-2.14 (m, 1H), 1.96 (s, 3H), 1.57-1.50 (m, 1H), 1.49 (s, 9H), 0.88 (d, 3H), 0.84 (d, 3H). LCMS: Rt=1.81 min, [M+H]+ 1238.

Workup

  1. concentrationconcentrated directly onto SiO2
  2. customchromatographed
  3. wash(gradient elution: 50-70% EtOAc/hexanes) which

Sources & evidence

ORD record
ord-50a78d54ec734778bc8c3dbb62b14fdb
Source dataset
uspto-grants-2010_12
Patent number
US07851439B2

Reaction notes

Loading…