1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 71522354, compound

HRID 1853973Notes

Reaction equation

HRID 1853973 reaction equation
[F:1][C:2]([F:10])([F:9])[CH2:3][CH2:4][CH2:5][C:6]([OH:8])=O.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C.Cl.[C:42]1([C:48]2[N:52]=[C:51]([CH:53]3[CH2:58][CH2:57][NH:56][CH2:55][CH2:54]3)[O:50][N:49]=2)[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>CN(C=O)C>[F:9][C:2]([F:1])([F:10])[CH2:3][CH2:4][CH2:5][C:6]([N:56]1[CH2:55][CH2:54][CH:53]([C:51]2[O:50][N:49]=[C:48]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[N:52]=2)[CH2:58][CH2:57]1)=[O:8]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27824465,5,5-trifluoropentanoic AcidHCID 222479254-(3-Phenyl-1,2,4-oxadiazol-5-yl)piperidine--hydrogen chloride (1/1)

Product 1

HCID 71522354HCID 71522354, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

5,5,5-Trifluoropentanoic acid (1.3 equiv), EDCI (1.3 equiv), HOBt (0.3 equiv) and diisopropylethylamine (4 equiv) were mixed in DMF (2 mL) for 5 minutes. 4-(3-Phenyl-[1,2,4]oxadiazol-5-yl)-piperidine hydrochloride (8c) (0.85 mmol, 1 equiv) was added with 3 mL of DMF. The reaction mixture was stirred overnight at room temperature and then evaporated under reduced pressure and purified by preparative HPLC. Yield 79%; 1H NMR (CDCl3) δ 8.06-8.09 (m, 2H), 7.48-7.51 (m, 3H), 4.49-4.54 (m, 1H), 3.90-3.94 (m, 1H), 3.24-3.33 (m, 2H), 2.97-3.06 (m, 1H), 2.46 (t, J=7.2 Hz, 2H), 2.17-2.24 (m, 4H), 1.93-1.98 (m, 4H). tR LCMS 6.0 min. Purity >99%; MS [M+H]+ m/z 368.

Workup

  1. customevaporated under reduced pressure
  2. custompurified by preparative HPLC
  3. customtR LCMS 6.0 min

Sources & evidence

ORD record
ord-5477fc982445494bb9e767ff9acb2be4
Source dataset
uspto-grants-2015_02
Patent number
US08962658B2

Reaction notes

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