Sodium Hydroxide → cyclopropyl(1,3-thiazol-2-yl)methanamine

HRID 874734Notes

Reaction equation

HRID 874734 reaction equation
[CH:1]1([C:4]([C:6]2[S:7][CH:8]=[CH:9][N:10]=2)=O)[CH2:3][CH2:2]1.[BH3-]C#[N:13].[Na+].[OH-].[Na+]>CO>[CH:1]1([CH:4]([C:6]2[S:7][CH:8]=[CH:9][N:10]=2)[NH2:13])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 224069281211508-19-8

Product 1

HCID 46785163cyclopropyl(1,3-thiazol-2-yl)methanamineYield 55%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was synthesized according to General Method F, utilizing cyclopropyl(thiazol-2-yl)methanone (0.28 g, 1.8 mmol), NH4OAc (1.7 g, 22 mmol), NaCNBH3 (0.46 g, 7.3 mmol), and MeOH (30 mL). Aq. NaOH (2 M, 15 mL) was added and the product was extracted into EtOAc (3×40 mL). The combined EtOAc layer was dried (MgSO4), filtered, concentrated to dryness. Purification by flash chromatography (Biotage Isolera, 25 g HP-SIL, 60-100% EtOAc in hexanes) gave the title compound as a yellow oil (0.15 g, 55% yield). 1H NMR (400 MHz, CDCl3) δ ppm 7.63 (d, J=2.8 Hz, 1H), 7.18 (d, J=2.8 Hz, 1H), 3.50 (d, J=8.5 Hz, 1H), 2.35 (br. s., 2H), 1.03-1.16 (m, 1H), 0.48-0.63 (m, 2H), 0.26-0.47 (m, 2H); MS ESI 138.0 [M-NH2]+, calcd for [C7H10N2S—NH2]+138.0.

Workup

  1. customThe title compound was synthesized
  2. extractionthe product was extracted into EtOAc (3×40 mL)
  3. dry with materialThe combined EtOAc layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customPurification by flash chromatography (Biotage Isolera, 25 g HP-SIL, 60-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-0717d05cd242466da2100dfc2a97a8a1
Source dataset
uspto-grants-2015_03
Patent number
US08980934B2

Reaction notes

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