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

HRID 1476780Notes

Reaction equation

HRID 1476780 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-6073fc2245234b6c9bb853bd197d1e98
Source dataset
uspto-grants-2016_08
Patent number
US09402833B2

Reaction notes

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