N-Methylethylamine → HCID 62798159, compound

HRID 1435605Notes

Reaction equation

HRID 1435605 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8]([OH:10])=O)[N:6]=1.[CH3:11][CH2:12][N:13]=[C:14]=NCCCN(C)C.C(NC)C>CN(C1C=CN=CC=1)C.CN(C=O)C>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8]([N:13]([CH2:12][CH3:11])[CH3:14])=[O:10])[N:6]=1

Participants

6

Reactant 3

HCID 12219N-MethylethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 34665(2-Amino-1,3-thiazol-4-yl)acetic acid

Product 1

HCID 62798159HCID 62798159, compoundYield 47.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

This compound was prepared from 2-amino-4-thiazoleacetic acid (3.48 g, 22 mmol), EDCI (4.37 g, 22.8 mmol), DMAP (270 mg, 2.2 mmol) and N-ethylmethylamine (1.99 mL, 23.2 mmol) in DMF (30 mL). The resulting solution was left overnight at room temperature. DMF was removed in vacuo and the residue purified by flash chromatrography on silica gel using 2% and 5% methanol/ethyl acetate as eluent. This procedure yielded 2.09 g (40%) of the title compound: 1H NMR (CDCl3) δ 6.28, 6.30 (1H), 5.06 (bs, 1H), 3.60, 3.61 (2H), 3.41 (m, 2H), 3.0, 2.92 (s, 3H), 1.11 (q, 3H). MS EI m/z 200.2.

Workup

  1. customDMF was removed in vacuo
  2. customthe residue purified by flash chromatrography on silica gel using 2% and 5% methanol/ethyl acetate as eluent

Sources & evidence

ORD record
ord-5883609fd60b499eb0126cbb5f0aa889
Source dataset
uspto-grants-2009_11
Patent number
US07618961B2

Reaction notes

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