Triethylamine → HCID 59369649, compound

HRID 45399Notes

Reaction equation

HRID 45399 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([NH2:16])=[N:13][C:12]=1[CH2:17][N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:24](Cl)(=[O:33])[CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(N(CC)CC)C>O1CCCC1.CN(C)C1C=CN=CC=1>[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([NH:16][C:24](=[O:33])[CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[N:13][C:12]=1[CH2:17][N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 64801Benzenepropanoyl chlorideHCID 866425232-Amino-4-morpholin-4-ylmethylthiazole-5-carboxylic acid benzylamide

Product 1

HCID 59369649HCID 59369649, compoundYield 74.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-amino-4-morpholin-4-ylmethylthiazole-5-carboxylic acid benzylamide (0.030 g, 0.09 mmol) in tetrahydrofuran (5 mL) at 0° C. was added hydrocinnamoyl chloride (0.1 mL, 0.67 mmol), 4-dimethylaminopyridine (catalytical amount) and triethylamine (0.2 mL, 1.4 mmol). The reaction mixture was allowed to warm to ambient temperature over 18 h then concentrated in vacuo. The crude product was purified by flash column chromatography eluting with ethyl acetate/hexanes (5/95 to 100/0) to afford the title compound (0.031 g); 1H NMR (DMSO-d6, 400 MHz) δ 7.40-7.15 (m, 10H), 4.46 (d, J=5.1 Hz, 2H), 3.62 (s, 2H), 3.19 (bs, 4H), 2.91 (t, J=7.6 Hz, 2H), 2.74 (t, J=8.1 Hz, 2H), 2.24 (br, s, 4H); MS (ES+) m/z 465 (M+1).

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe crude product was purified by flash column chromatography
  3. washeluting with ethyl acetate/hexanes (5/95 to 100/0)

Sources & evidence

ORD record
ord-fc9dc78fab284c02b4fa0fec7a35e31b
Source dataset
uspto-grants-2013_09
Patent number
US08541457B2

Reaction notes

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