4-Thiazoleacetic acid, 2-amino-, ethyl ester → HCID 86612282, compound

HRID 1191701Notes

Reaction equation

HRID 1191701 reaction equation
COC(=O)C1C=CC(N[C:11](=[O:31])[CH2:12][S:13][CH:14]2[C:18]([CH3:19])=[C:17]([CH3:20])[C:16](=[O:21])[N:15]2[CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)=NC=1.[CH2:33]([O:35][C:36](=[O:44])[CH2:37][C:38]1[N:39]=[C:40]([NH2:43])[S:41][CH:42]=1)[CH3:34]>>[CH2:33]([O:35][C:36](=[O:44])[CH2:37][C:38]1[N:39]=[C:40]([NH:43][C:11](=[O:31])[CH2:12][S:13][CH:14]2[C:18]([CH3:19])=[C:17]([CH3:20])[C:16](=[O:21])[N:15]2[CH2:22][C:23]2[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=2)[S:41][CH:42]=1)[CH3:34]

Participants

3

Reactant 2

HCID 1044544-Thiazoleacetic acid, 2-amino-, ethyl esterHCID 16058694HCID 16058694, compound

Product 1

HCID 86612282HCID 86612282, compound

Procedure

The product from Example 1, Part C (160 mg, 0.5 mmol) and (2-aminothiazol-4-yl)-acetic acid ethyl ester (92 mg, 0.5 mmol) were reacted as described in Example 5. After evaporation of the reaction solvent the residue was partitioned between water and EtOAc, and the organic phase was washed with EtOAc. The combined organics were washed with brine, dried (Na2SO4), filtered, and evaporated. The title compound was obtained by silica gel chromatography (90 mg, 37%). 1H NMR (400 MHz, CDCl3) δ 9.80 (br s, 1H), 7.22 (d, J=8 Hz, 2H), 6.83 (d, J=8 Hz, 2H), 6.80 (s, 1H), 5.19 (d, J=15 Hz, 1H), 4.60 (s, 1H), 4.15 (m, 3H), 3.77 (s, 3H), 3.61 (s, 3H), 3.06 (d, J=16 Hz, 1H), 2.98 (d, J=16 Hz, 1H), 1.90 (s, 3H), 1.81 (s, 3H). MS: m/z (MH+) 490.

Workup

  1. customAfter evaporation of the reaction solvent the residue
  2. customwas partitioned between water and EtOAc
  3. washthe organic phase was washed with EtOAc
  4. washThe combined organics were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-400b79bea2544a71a3f604c844b992d7
Source dataset
uspto-grants-2014_03
Patent number
US08680122B2

Reaction notes

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