1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 54670254, compound

HRID 1426907Notes

Reaction equation

HRID 1426907 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[N:11]=[C:10]([C@H:12]2[CH2:16][CH2:15][CH2:14][N:13]2[C:17]2[CH:22]=[CH:21][N:20]3[N:23]=[CH:24][C:25]([C:26](O)=[O:27])=[C:19]3[N:18]=2)[CH:9]=[CH:8][CH:7]=1.CN(C=O)C.C(Cl)Cl.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CCOC(C)=O>[C:17]12[CH:22]=[CH:21][N:20]3[C:19]([N:18]=1)=[C:25]([CH:24]=[N:23]3)[C:26](=[O:27])[NH:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[N:11]=[C:10]([CH:9]=[CH:8][CH:7]=1)[C@@H:12]1[N:13]2[CH2:14][CH2:15][CH2:16]1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 22350042dichloromethane N,N-dimethylformamideHCID 67471093HCID 67471093, compound

Product 1

HCID 54670254HCID 54670254, compoundYield 45.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (R)-5-(2-(6-(3-aminopropoxy)pyridin-2-yl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (70 mg, 0.18 mmol) in 1:2 DMF/DCM (9 mL) was added EDCI (110 mg, 0.55 mmol) followed by HOBT (74 mg, 0.55 mmol) at ambient temperature. After stirring for 10 minutes, TEA (0.077 mL, 0.55 mmol) was added to the reaction mixture and stirred for 6 hours. The reaction mixture was diluted with EtOAc, washed with saturated NH4Cl, saturated NaHCO3, and brine, then dried (MgSO4), filtered, and concentrated. The crude material was purified by silica column chromatography, eluting with 2% MeOH/DCM to yield the title product (30 mg, 45% yield). MS (apci) m/z=365.2 (M+H).

Workup

  1. stirringstirred for 6 hours
  2. washwashed with saturated NH4Cl, saturated NaHCO3, and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by silica column chromatography
  7. washeluting with 2% MeOH/DCM

Sources & evidence

ORD record
ord-469d1f5868ba40a19cd71e1559b121df
Source dataset
uspto-grants-2015_01
Patent number
US08933084B2

Reaction notes

Loading…