1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 71522353, compound

HRID 1853972Notes

Reaction equation

HRID 1853972 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.[CH:22]1[CH:23]=[CH:24]C2N(O)N=[N:28][C:26]=2[CH:27]=1.C(N(C(C)C)CC)(C)C.[S:41]1[CH:45]=[CH:44][CH:43]=[C:42]1[C:46]1[N:50]=[C:49](N2CCCCC2)[O:48][N:47]=1>CN(C=O)C>[F:9][C:2]([F:1])([F:10])[CH2:3][CH2:4][CH2:5][C:6]([N:28]1[CH2:24][CH2:23][CH:22]([C:49]2[O:48][N:47]=[C:46]([C:42]3[S:41][CH:45]=[CH:44][CH:43]=3)[N:50]=2)[CH2:27][CH2:26]1)=[O:8]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27824465,5,5-trifluoropentanoic AcidHCID 131732501HCID 131732501, compound

Product 1

HCID 71522353HCID 71522353, compoundYield 83%

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-(thien-2-yl)-1,2,4-oxadiazol-5-yl]-piperidine (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 83%; 1H NMR (CD2Cl2) δ 7.80 (dd, J=1.2 Hz, J=3.6 Hz, 1H), 7.56 (dd, J=1.2 Hz, J=5.0 Hz, 1H), 7.19 (dd, J=3.6 Hz, J=5.0 Hz, 1H), 4.48-4.55 (m, 1H), 3.87-3.95 (m, 1H), 3.19-3.33 (m, 2H), 2.89-3.00 (m, 1H), 2.44 (t, J=7.3 Hz, 2H), 2.15-2.31 (m, 4H), 1.86-1.96 (m, 4H). tR LCMS 6.1 min. Purity >99%; MS [M+H]+ m/z 374.

Workup

  1. customevaporated under reduced pressure
  2. custompurified by preparative HPLC
  3. customtR LCMS 6.1 min

Sources & evidence

ORD record
ord-7f062dac2387461d824e7a0afbd0c8a9
Source dataset
uspto-grants-2015_02
Patent number
US08962658B2

Reaction notes

Loading…