Calcium Carbonate → HCID 58770016, compound

HRID 657207Notes

Reaction equation

HRID 657207 reaction equation
[CH:1]1([O:5][C:6]2[N:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=2)[CH2:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[Ca+2].Cl[C:19]([O:21][C:22]1[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=1)=[O:20].C(Cl)Cl.CO>C1(C)C=CC=CC=1>[N+:28]([C:25]1[CH:24]=[CH:23][C:22]([O:21][C:19](=[O:20])[NH:12][C:9]2[CH:10]=[N:11][C:6]([O:5][CH:1]3[CH2:2][CH2:3][CH2:4]3)=[CH:7][CH:8]=2)=[CH:27][CH:26]=1)([O-:30])=[O:29]

Participants

6

Reactant 4

HCID 10112Calcium CarbonateHCID 821294-Nitrophenyl chloroformateHCID 21226129Dichloromethane methanol2×HCID 587700226-Cyclobutoxypyridin-3-amine

Product 1

HCID 58770016HCID 58770016, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 6-cyclobutoxy-pyridin-3-ylamine (4.41 g, assume 25 mmol), as prepared in the previous step, and CaCO3 (3.25 g, 32.5 mmol) (10 micron powder) was treated with a homogeneous solution of 4-nitrophenyl chloroformate (5.54 g, 27.5 mmol) in toluene (28 mL) in one portion at rt, and was stirred at “rt” (reaction warmed spontaneously) for 2 h. The reaction mixture was then directly loaded onto a flash silica column (95:5 DCM/MeOH→9:1 DCM/MeOH) to afford 5.65 g of material, which was further purified by trituration with hot toluene (1×200 mL) to provide the title compound (4.45 g, 54%). 1H NMR (400 MHz, CDCl3) δ 8.28 (m, 2H), 8.12 (d, 1H), 7.81 (m, 1H), 7.39 (m, 2H), 6.85 (br s, 1H), 6.72 (d, 1H), 5.14 (m, 1H), 2.45 (m, 2H), 2.13 (m, 2H), 1.84 (m, 1H), 1.68 (m, 1H). LC-MS (ESI): calcd mass 329.1, found 330.1 (MH+).

Workup

  1. customreaction
  2. temperaturewarmed spontaneously) for 2 h

Sources & evidence

ORD record
ord-ee5a79fd3efe4d73af7e986fe4d2b77f
Source dataset
uspto-grants-2011_12
Patent number
US08071768B2

Reaction notes

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