1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 118047278, compound

HRID 63838Notes

Reaction equation

HRID 63838 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2([C:27]([F:30])([F:29])[F:28])[O:16][CH2:15][N:14]=[C:13]2[C:17]2[CH:25]=[CH:24][C:20]([C:21](O)=[O:22])=[C:19]([CH3:26])[CH:18]=2)[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[NH2:52][N:53]1[CH2:58][CH2:57][CH2:56][N:55]([CH2:59][C:60]([F:63])([F:62])[F:61])[C:54]1=[O:64]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2([C:27]([F:28])([F:29])[F:30])[O:16][CH2:15][N:14]=[C:13]2[C:17]2[CH:25]=[CH:24][C:20]([C:21]([NH:52][N:53]3[CH2:58][CH2:57][CH2:56][N:55]([CH2:59][C:60]([F:61])([F:63])[F:62])[C:54]3=[O:64])=[O:22])=[C:19]([CH3:26])[CH:18]=2)[CH:5]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:7]=1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 1180467991-Amino-3-(2,2,2-trifluoroethyl)-1,3-diazinan-2-oneHCID 1180473674-[5-[3-Chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-2,5-dihydro-1,3-oxazol-4-yl]-2-methylbenzoic acid

Product 1

HCID 118047278HCID 118047278, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Into a 50-mL round-bottom flask, was placed 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-2,5-dihydro-1,3-oxazol-4-yl]-2-methylbenzoic acid (50 mg, 0.11 mmol, 1.00 equiv), dichloromethane (20 mL), EDCI (25 mg, 0.13 mmol, 1.20 equiv), HOBt (18 mg, 0.13 mmol, 1.20 equiv), TEA (30 mg, 0.30 mmol, 3.00 equiv), 1-amino-3-(2,2,2-trifluoroethyl)-1,3-diazinan-2-one (22 mg, 0.11 mmol, 1.00 equiv). The resulting solution was stirred overnight at room temperature. The resulting solution was diluted with 40 mL of DCM. The resulting mixture was washed with 3×20 mL of brine. The mixture was dried over anhydrous sodium sulfate. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:1). This resulted in 12 mg (17.2%) of 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-2,5-dihydro-1,3-oxazol-4-yl]-2-methyl-N-[2-oxo-3-(2,2,2-trifluoroethyl)-1,3-diazinan-1-yl]benzamide as a white solid. (ES, m/z): 631 [M+H]+ 1H-NMR (CDCl3, ppm): 7.82 (s, 1H), 7.76-7.73 (m, 2H), 7.69 (s, 1H), 7.61-7.50 (m, 3H), 4.14 (d, J=18.6 Hz, 1H), 4.07-3.98 (m, 2H), 3.80-3.69 (m, 3H), 3.58-3.52 (m, 2H), 2.51 (s, 3H), 2.25-2.17 (m, 2H).

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. washThe resulting mixture was washed with 3×20 mL of brine
  3. dry with materialThe mixture was dried over anhydrous sodium sulfate
  4. concentrationThe resulting mixture was concentrated under vacuum
  5. customThis resulted in 12 mg (17.2%) of 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-2,5-dihydro-1,3-oxazol-4-yl]-2-methyl-N-[2-oxo-3-(2,2,2-trifluoroethyl)-1,3-diazinan-1-yl]benzamide as a white solid

Sources & evidence

ORD record
ord-5058aec5b6574f028eac885a7ce78eac
Source dataset
uspto-grants-2016_09
Patent number
US09447084B2

Reaction notes

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