1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 71599525, compound

HRID 2167747Notes

Reaction equation

HRID 2167747 reaction equation
CCN=C=NCCCN(C)C.[F:12][C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=1[C@H:20]1[CH2:24][CH2:23][CH2:22][N:21]1[C:25]1[CH:30]=[CH:29][N:28]2[N:31]=[CH:32][C:33]([C:34](O)=[O:35])=[C:27]2[CH:26]=1.[F:37][C:38]1[CH:43]=[CH:42][C:41]([S:44]([NH2:47])(=[O:46])=[O:45])=[CH:40][CH:39]=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[F:12][C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=1[C@H:20]1[CH2:24][CH2:23][CH2:22][N:21]1[C:25]1[CH:30]=[CH:29][N:28]2[N:31]=[CH:32][C:33]([C:34]([NH:47][S:44]([C:41]3[CH:40]=[CH:39][C:38]([F:37])=[CH:43][CH:42]=3)(=[O:46])=[O:45])=[O:35])=[C:27]2[CH:26]=1

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 1202314-FluorobenzenesulfonamideHCID 89618448HCID 89618448, compound

Product 1

HCID 71599525HCID 71599525, compoundYield 6.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

EDCI (111 mg, 0.5 mmol) was added to a solution of (R)-5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyridine-3-carboxylic acid (100 mg, 0.29 mmol) in DCM (4 mL) followed by DMAP (36 mg, 0.29 mmol) and 4-fluorobenzenesulfonamide (56 mg, 0.31 mmol) and stirring was continued at 20-35° C. for 20 h. Reaction mixture was quenched with water, extracted into EtOAc, dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford the crude. The crude compound was purified by Preparative HPLC [Column: 21.2×150×5 um, Zorbax, Eclipse, C-18, Mobile phase-A: Water, B:ACN, Gradient (Time/% B): 0/30, 2/40, 10/80 and Flow rate: 20 mL/min] to afford 9.3 mg of the title compound.

Workup

  1. customReaction mixture
  2. customwas quenched with water
  3. extractionextracted into EtOAc
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customto afford the crude
  7. customThe crude compound was purified by Preparative HPLC [Column: 21.2×150×5 um, Zorbax, Eclipse, C-18, Mobile phase-A: Water, B:ACN, Gradient (Time/% B): 0/30, 2/40, 10/80 and Flow rate: 20 mL/min]

Sources & evidence

ORD record
ord-4c477778c9464704ad0da3ae6f0f7a8b
Source dataset
uspto-grants-2015_06
Patent number
US09045478B2

Reaction notes

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