1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Tmp269

HRID 1397207Notes

Reaction equation

HRID 1397207 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[O:7][N:6]=[C:5]([C:8]2[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=2)[C:11]([OH:13])=O)[N:4]=1.[C:19]1([C:25]2[N:26]=[C:27]([C:30]3([CH2:36][NH2:37])[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)[S:28][CH:29]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CCN=C=NCCCN(C)C>C(Cl)Cl>[C:19]1([C:25]2[N:26]=[C:27]([C:30]3([CH2:36][NH:37][C:11](=[O:13])[C:10]4[CH:14]=[CH:15][CH:16]=[C:8]([C:5]5[N:4]=[C:3]([C:2]([F:1])([F:18])[F:17])[O:7][N:6]=5)[CH:9]=4)[CH2:31][CH2:32][O:33][CH2:34][CH2:35]3)[S:28][CH:29]=2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 251808543-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acidHCID 67322930(4-(4-phenylthiazol-2-yl)tetrahydro-2H-pyran-4-yl)methanamine

Product 1

HCID 53344908Tmp269

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid (52 mg, 0.202 mmole), (4-(4-phenylthiazol-2-yl)tetrahydro-2H-pyran-4-yl)methanamine (50 mg, 0.184 mmole), and EDCI (38.5 mg, 0.202 mmole) in CH2Cl2 (2 ml) was stirred at room temperature for 8 h. The reaction mixture was then diluted with methylene chloride (10 ml), washed with water (5 ml), dried over MgSO4 and concentrated under reduced pressure. The residue was purified by ISCO (silica gel, elute: 2% methanol in CH2Cl2) to give N-((4-(4-phenylthiazol-2-yl)tetrahydro-2H-pyran-4-yl)methyl)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide as a white solid product (59 mg, 62% yield): 1H NMR (CDCl3, 500 MHz): 8.49 (s, 1H), 8.22 (d, J=7.5 Hz, 1H), 7.98 (d, J=8.5 Hz, 1H), 7.88 (d, J=8 Hz, 2H), 7.56-7.53 (m, 2H), 7.52 (s, 1H), 7.369-7.31 (m, 3H), 3.97-3.93 (m, 2H), 3.91 (d, J=5.5 Hz, 2H), 3.77-3.74 (m, 2H), 2.36-2.28 (m, 2H), 2.06-2.04 (m, 2H). MS (ESI) m/z: Calculated for C25H21F3N4O3S: 514.13. found: 515.1 (M−H)+.

Workup

  1. washwashed with water (5 ml)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by ISCO (silica gel, elute: 2% methanol in CH2Cl2)

Sources & evidence

ORD record
ord-f16f96d44558484a9a9cdbe6734116e8
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

Loading…