1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 71522355, compound

HRID 1853974Notes

Reaction equation

HRID 1853974 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.[CH3:41][S:42]([C:45]1[CH:50]=[CH:49][C:48]([C:51]2[N:55]=[C:54]([CH:56]3[CH2:61][CH2:60][NH:59][CH2:58][CH2:57]3)[O:53][N:52]=2)=[CH:47][CH:46]=1)(=[O:44])=[O:43]>CN(C=O)C>[F:9][C:2]([F:1])([F:10])[CH2:3][CH2:4][CH2:5][C:6]([N:59]1[CH2:58][CH2:57][CH:56]([C:54]2[O:53][N:52]=[C:51]([C:48]3[CH:49]=[CH:50][C:45]([S:42]([CH3:41])(=[O:43])=[O:44])=[CH:46][CH:47]=3)[N:55]=2)[CH2:61][CH2:60]1)=[O:8]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27611494-{3-[4-(Methanesulfonyl)phenyl]-1,2,4-oxadiazol-5-yl}piperidineHCID 27824465,5,5-trifluoropentanoic Acid

Product 1

HCID 71522355HCID 71522355, compoundYield 69%

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-[4-(methylsulfonyl)phenyl-]1,2,4-oxadiazol-5-yl]piperidine (34c) (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 69%; 1H NMR (CD2Cl2) δ 8.32 (d, J=8.7 Hz, 2H), 8.08 (d, J=8.7 Hz, 2H), 4.52-4.57 (m, 1H), 3.92-3.96 (m, 1H), 3.23-3.39 (m, 2H), 3.11 (s, 3H), 2.92-3.01 (m, 1H), 2.46 (t, J=7.2 Hz, 2H), 2.16-2.32 (m, 4H), 1.82-2.01 (m, 4H). tR LCMS 5.7 min. Purity >99%; MS [M+H]+ m/z 446.

Workup

  1. customevaporated under reduced pressure
  2. custompurified by preparative HPLC
  3. customtR LCMS 5.7 min

Sources & evidence

ORD record
ord-690e1345549b4295a5deac36a3364282
Source dataset
uspto-grants-2015_02
Patent number
US08962658B2

Reaction notes

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