1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-((1R)-6-(2-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl)-1,2,3,4-tetrahydronaphthalen-1-yl)-2-(3-oxo-1-tosylpiperazin-2-yl)acetamide

HRID 747059Notes

Reaction equation

HRID 747059 reaction equation
[CH3:1][C:2]1[N:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[C@H:19]([NH2:23])[CH2:18][CH2:17][CH2:16]3)[O:4][N:3]=1.[O:24]=[C:25]1[NH:30][CH2:29][CH2:28][N:27]([S:31]([C:34]2[CH:40]=[CH:39][C:37]([CH3:38])=[CH:36][CH:35]=2)(=[O:33])=[O:32])[CH:26]1[CH2:41][C:42](O)=[O:43].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH3:1][C:2]1[N:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[C@H:19]([NH:23][C:42](=[O:43])[CH2:41][CH:26]2[C:25](=[O:24])[NH:30][CH2:29][CH2:28][N:27]2[S:31]([C:34]2[CH:40]=[CH:39][C:37]([CH3:38])=[CH:36][CH:35]=2)(=[O:33])=[O:32])[CH2:18][CH2:17][CH2:16]3)[O:4][N:3]=1

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 620340531-[(4-methylphenyl)sulfonyl]-3-oxo-2-Piperazineacetic acidHCID 69078045(1R)-6-(2-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl)-1,2,3,4-tetrahydronaphthalen-1-amine

Product 1

HCID 11250383N-((1R)-6-(2-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl)-1,2,3,4-tetrahydronaphthalen-1-yl)-2-(3-oxo-1-tosylpiperazin-2-yl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 100 mL round bottom flask was added (1R)-6-(2-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl)-1,2,3,4-tetrahydronaphthalen-1-amine (25.0 mg, 0.06 mmol), followed by 2-(3-oxo-1-tosylpiperazin-2-yl)acetic acid (50 mg, 0.016 mmol), dry CH2Cl2 (10 mL), HATU (12 mg, 0.03 mmol), EDCI (13 mg, 0.068 mmol) and hunig base (0.022 mL, 0.123 mmol). The resulting mixture was stirred at rt for 20 h. Removed solvent to dryness. Solvent was removed. The residue was purified by chromatography on silica gel. Elution with CH2Cl2:MeOH mixture (97:3) gave final compound. MS m/z: 600.3 (M+H). Calc'd. for C32H33N5O5S -599.71.s

Workup

  1. customSolvent was removed
  2. customThe residue was purified by chromatography on silica gel
  3. washElution with CH2Cl2

Sources & evidence

ORD record
ord-e794a0f63a3e44afa4605e71b2873f10
Source dataset
uspto-grants-2008_07
Patent number
US07393852B2

Reaction notes

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