Methyl chloroformate → [5-(3-Isopropyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-carbamic acid methyl ester

HRID 336405Notes

Reaction equation

HRID 336405 reaction equation
[CH3:1][CH:2]([C:4]1[CH:5]=[C:6]([C:10]2[N:15]3[N:16]=[C:17]([NH2:19])[N:18]=[C:14]3[CH:13]=[CH:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1)[CH3:3].Cl[C:21]([O:23][CH3:24])=[O:22]>N1C=CC=CC=1>[CH3:24][O:23][C:21](=[O:22])[NH:19][C:17]1[N:18]=[C:14]2[CH:13]=[CH:12][CH:11]=[C:10]([C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([CH:2]([CH3:1])[CH3:3])[CH:5]=3)[N:15]2[N:16]=1

Participants

4

Reactant 2

HCID 6586Methyl chloroformateHCID 445561185-[3-(Propan-2-yl)phenyl][1,2,4]triazolo[1,5-a]pyridin-2-amine

Product 1

HCID 59186194[5-(3-Isopropyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-carbamic acid methyl esterYield 61%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 5-[3-(propan-2-yl)phenyl][1,2,4]triazolo[1,5-a]pyridin-2-amine (23.6 mg, 0.0935 mmol, 1 equiv) in pyridine was added methyl chloroformate (36.1 uL, 0.468 mmol, 5.00 equiv) at 24° C. After 3 h, the reaction mixture was concentrated in vacuo. The resulting residue was partitioned between saturated aqueous sodium bicarbonate solution (5 mL) and ethyl acetate (5 mL). The aqueous layer was extracted with ethyl acetate (2×5 mL). The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated. Purification by preparative HPLC provided a white solid (17.7 mg, 61%). LCMS (ESI) m/z: 311.2. 1H NMR (500 MHz, DMSO-d6), δ: 10.45 (s, 1H), 7.88 (m, 1H), 7.81 (m, 1H), 7.65-7.72 (m, 2H), 7.48 (t, J=7.6 Hz, 1H), 7.42 (m, 1H), 7.28 (dd, J=7.0, 1.6 Hz, 1H), 3.67 (s, 3H), 3.00 (m, 1H), 1.28 (d, J=6.9 Hz, 6H).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customThe resulting residue was partitioned between saturated aqueous sodium bicarbonate solution (5 mL) and ethyl acetate (5 mL)
  3. extractionThe aqueous layer was extracted with ethyl acetate (2×5 mL)
  4. dry with materialThe combined organic extracts were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-d1d8edfee7f24ebd968e243f660485e8
Source dataset
uspto-grants-2014_11
Patent number
US08889673B2

Reaction notes

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