Dimethylamine, hydrochloride → 5-((R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl)-N-(3-(dimethylcarbamoyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-6-yl)pyrazolo[1,5-a]pyridine-3-carboxamide

HRID 926733Notes

Reaction equation

HRID 926733 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C@H:9]1[CH2:13][CH2:12][CH2:11][N:10]1[C:14]1[CH:19]=[CH:18][N:17]2[N:20]=[CH:21][C:22]([C:23]([NH:25][CH:26]3[CH2:31][N:30]4[N:32]=[CH:33][C:34]([C:35]([OH:37])=O)=[C:29]4[CH2:28][CH2:27]3)=[O:24])=[C:16]2[CH:15]=1.C[CH2:39][N:40]=[C:41]=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.Cl.CNC.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C@H:9]1[CH2:13][CH2:12][CH2:11][N:10]1[C:14]1[CH:19]=[CH:18][N:17]2[N:20]=[CH:21][C:22]([C:23]([NH:25][CH:26]3[CH2:31][N:30]4[N:32]=[CH:33][C:34]([C:35](=[O:37])[N:40]([CH3:41])[CH3:39])=[C:29]4[CH2:28][CH2:27]3)=[O:24])=[C:16]2[CH:15]=1

Participants

8

Reactant 5

HCID 10473Dimethylamine, hydrochlorideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 89618999HCID 89618999, compound

Product 1

HCID 715992645-((R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl)-N-(3-(dimethylcarbamoyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-6-yl)pyrazolo[1,5-a]pyridine-3-carboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 6-(5-((R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyridine-3-carboxamido)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine-3-carboxylic acid (45 mg, 0.08 mmol) in dry DMF (1 mL) was added EDCI (28.7 mg, 0.09 mmol), HOBt (12 mg, 0.88 mmol) and stirring was continued at 25° C. for 15 min. To the above reaction added dimethylamine hydrochloride (7.8 mg, 0.1 mmol) followed by DIPEA (0.05 ml, 0.26 mmol), stirring was continued at 25° C. for 16 h. Reaction mixture was diluted with DCM (50 mL), washed it with water followed by brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford title compound as white solid. MS (ESI): m/z 534.2 (M+H).

Workup

  1. customTo the above reaction
  2. stirringstirring
  3. waitwas continued at 25° C. for 16 h
  4. customReaction mixture
  5. washwashed it with water
  6. dry with materialdried over anhydrous sodium sulphate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e89c674daa5b4511b63eefefe27db880
Source dataset
uspto-grants-2016_03
Patent number
US09289419B2

Reaction notes

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