1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 45274931, compound

HRID 1667204Notes

Reaction equation

HRID 1667204 reaction equation
C(N=C=NCCCN(C)C)C.[O:12]=[C:13]1[C:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:17][CH2:16][CH2:15][N:14]1[CH2:31][C:32](O)=[O:33].[NH:35]1[CH2:40][CH2:39][CH:38]([N:41]2[C:45]3[CH:46]=[CH:47][C:48]([C:50]([F:53])([F:52])[F:51])=[CH:49][C:44]=3[N:43]=[N:42]2)[CH2:37][CH2:36]1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[O:33]=[C:32]([N:35]1[CH2:40][CH2:39][CH:38]([N:41]2[C:45]3[CH:46]=[CH:47][C:48]([C:50]([F:53])([F:51])[F:52])=[CH:49][C:44]=3[N:43]=[N:42]2)[CH2:37][CH2:36]1)[CH2:31][N:14]1[CH2:15][CH2:16][CH2:17][C:18]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]1=[O:12]

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 2777431HCID 2777431, compoundHCID 673592802-(2-Oxo-3,3-diphenylpiperidin-1-yl)acetic acid

Product 1

HCID 45274931HCID 45274931, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

N1-((Ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine (0.132 mL, 0.743 mmol) was added via syringe to a mixture of the product of Example 68E (230 mg, 0.743 mmol), 1-(piperidin-4-yl)-5-(trifluoromethyl)-1H-benzo[d][1,2,3]triazole (201 mg, 0.743 mmol), and 4-(dimethylamino)pyridine (9.1 mg, 0.07 mmol) in CH2Cl2 (3 mL). The reaction was allowed to proceed at ambient temperature for 23 hours. The reaction mixture was diluted with CH2Cl2 (50 mL) and washed with 1 N aqueous HCl, saturated aqueous NaHCO3 solution and brine, dried with Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by chromatography on silica gel (Analogix® Intelliflash™ 280; SF15-24 g column; 50%-100% ethyl acetate/hexanes, 0-20 minutes, 30 mL/minute) to yield an amorphous solid which was triturated with 12 mL 1:1 ether/hexanes and 2 mL ether. The solid was collected by vacuum filtration and air-dried to afford the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 8.37 (s, 1H), 7.73 (d, J=8.7, 1H), 7.51 (d, J=8.4, 1H), 7.39-7.14 (m, 10H), 5.10-4.95 (m, 1H), 4.82-4.66 (m, 1H), 4.34 (d, J=15.1, 1H), 4.27-4.06 (m, 2H), 3.71-3.50 (m, 2H), 3.46-3.29 (m, 1H), 3.14-2.94 (m, 1H), 2.73-2.63 (m, 2H), 2.64-2.47 (m, 1H), 2.44-2.14 (m, 3H), 1.96-1.82 (m, 2H). MS (ESI+) m/z 562 (M+H)+.

Workup

  1. washwashed with 1 N aqueous HCl, saturated aqueous NaHCO3 solution and brine
  2. dry with materialdried with Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by chromatography on silica gel (Analogix® Intelliflash™ 280; SF15-24 g column; 50%-100% ethyl acetate/hexanes, 0-20 minutes, 30 mL/minute)
  6. customto yield an amorphous solid which
  7. customwas triturated with 12 mL 1:1 ether/hexanes and 2 mL ether
  8. filtrationThe solid was collected by vacuum filtration
  9. customair-dried

Sources & evidence

ORD record
ord-36b69792242a48b0874eff1eface0706
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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