Pyridine → HCID 90427244, compound

HRID 2279006Notes

Reaction equation

HRID 2279006 reaction equation
Cl.[CH3:2][O:3][CH2:4][C@H:5]([NH2:7])[CH3:6].N1C=CC=CC=1.[Cl:14][CH2:15][CH2:16][N:17]=[C:18]=[O:19]>C1COCC1>[Cl:14][CH2:15][CH2:16][NH:17][C:18]([NH:7][C@@H:5]([CH3:6])[CH2:4][O:3][CH3:2])=[O:19]

Participants

5

Reactant 3

HCID 1049PyridineHCID 160352-Chloroethyl isocyanateHCID 53350298(2R)-1-Methoxypropan-2-amine--hydrogen chloride (1/1)

Product 1

HCID 90427244HCID 90427244, compoundYield 50.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (R)-1-methoxypropan-2-amine hydrochloride (500 mg, 3.98 mmol) and pyridine (315 mg, 3.98 mmol) in THF (15 mL) was treated drop-wise with 2-chloroethylisocyanate (420 mg, 3.98 mmol) and stirred at RT overnight. The mixture was concentrated to dryness, partitioned between EtOAc and brine and the organic layer dried over Na2SO4 and concentrated to dryness to afford (S)-1-(2-chloroethyl)-3-(1-methoxypropan-2-yl)urea (393 mg, 50%). 1H NMR (400 MHz, DMSO-d6): δ 6.08 (s, 1 H), 5.93 (d, J=8.1 Hz, 1 H), 3.71 (m, 1 H), 3.56-3.51 (m, 3 H), 3.30-3.23 (m, 3 H), 3.22 (s, 3 H), 0.98 (d, J=6.7 Hz, 3H).

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. custompartitioned between EtOAc and brine
  3. dry with materialthe organic layer dried over Na2SO4
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-8db5a649cc88462caa8ec584215f3dd9
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

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