2-Aminothiazole → HCID 24960867, compound

HRID 1430642Notes

Reaction equation

HRID 1430642 reaction equation
[F:1][C:2]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:3]=1[O:4][C:5]([C:10]1[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=1)([CH3:9])[C:6](O)=[O:7].[NH2:25][C:26]1[S:27][CH:28]=[CH:29][N:30]=1.CCN=C=NCCCN(C)C.C(N(CC)CC)C>C(Cl)Cl>[F:1][C:2]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:3]=1[O:4][C:5]([C:10]1[CH:11]=[CH:12][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:14][CH:15]=1)([CH3:9])[C:6]([NH:25][C:26]1[S:27][CH:28]=[CH:29][N:30]=1)=[O:7]

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 59363828HCID 59363828, compound

Product 1

HCID 24960867HCID 24960867, compoundYield 52.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 2-(2,4-Difluoro-phenoxy)-2-(4-methanesulfonyl-phenyl)-propionic acid (0.184 g, 0.52 mmol), 2-aminothiazole (0.59 g, 0.60 mmol) HOBt (0.070 g, 0.52 mmol), and EDCI 0.10 g, 0.52 mmol) in methylene dichloride (10 ml) was added triethyl amine (0.06 g, 0.59 mmol). The resulting mixture was stirred at room temperature for overnight followed by dilution with 10 ml methylene dichloride. The reaction mixture was poured onto water (20 ml), and organic layer separated, washed with water (2×20 ml), brine (20 ml), dried over sodium sulfate and solvent evaporated to get residue which was purified by preparative TLC using 50% ethyl acetate in hexane as mobile phase to give the desired compound (0.12 g). 1H NMR (400 MHz, CDCl3): δ 1.90 (s, 3H), 3.08 (s, 3H), 6.64-6.71 (m, 2H), 6.94 (m, 1H), 7.05 (d, J=3.6 Hz, 1H), 7.51 (d, J=3.6 Hz, 1H), 7.86 (d, J=8.4 Hz, 2H), 8.01 (d, J=8.4 Hz, 2H), 10.20 (s, 1H); MS (EI) m/z: 439.00 (M+1); mp: 89-90° C.

Workup

  1. additionThe reaction mixture was poured onto water (20 ml), and organic layer
  2. customseparated
  3. washwashed with water (2×20 ml), brine (20 ml)
  4. dry with materialdried over sodium sulfate and solvent
  5. customevaporated
  6. customto get residue which
  7. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-d1bc037f33904da98c80325ef59f4481
Source dataset
uspto-grants-2015_01
Patent number
US08940900B2

Reaction notes

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