1,2-Dichloroethane → HCID 178511187, compound

HRID 2204660Notes

Reaction equation

HRID 2204660 reaction equation
[C:1]([CH2:3][C:4]([OH:6])=O)#[N:2].[CH2:7](Cl)[CH2:8]Cl.[CH:11]1[CH:12]=[CH:13][C:14]2[N:19](O)[N:18]=[N:17][C:15]=2[CH:16]=1.[C:21]([CH2:23][C:24](OC1C(F)=C(F)C(F)=C(F)C=1F)=O)#[N:22].C[N:39]([CH:41]=O)[CH3:40]>>[C:1]([CH2:3][C:4]([NH:19][C@@H:14]1[CH2:8][CH2:7][C@H:12]([C:11]2[C:16]3=[C:24]4[CH:23]=[CH:21][NH:22][C:40]4=[N:39][CH:41]=[C:15]3[NH:17][N:18]=2)[CH2:13]1)=[O:6])#[N:2]

Participants

6

Reactant 5

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 9740Cyanoacetic acidHCID 757711-HydroxybenzotriazoleHCID 20402415Perfluorophenyl 2-cyanoacetate

Product 1

HCID 178511187HCID 178511187, compoundYield 9%

Procedure

(3R)-(3,6-Dihydropyrazolo[4,3-d]pyrrolo[2,3-b]pyridin-1-yl)cyclopentanamine (0.12 g, 0.48 mmol, Preparation #29) and 2-cyanoacetic acid (0.042 g, 0.48 mmol), were combined in DMF (6.0 mL) with EDC (0.12 g, 0.65 mmol) and HOBt (0.076 g, 0.48 mmol). The mixture was stirred for about 3 h at room temperature. Perfluorophenyl 2-cyanoacetate (0.62 g, 2.5 mmol, Preparation #6) was added and the reaction mixture was stirred for about 48 h at room temperature. The solvent was removed under reduced pressure and the crude material was purified by RP-HPLC (Table 2, Method q) to give 2-cyano-N-((1R,3S)-3-(3,6-dihydropyrazolo[4,3-d]pyrrolo[2,3-b]pyridin-1-yl)cyclopentyl)acetamide (0.014 g, 9%): LC/MS (Table 2, Method a) Rt=1.52 min; m/z: 307 (M−H)−.

Workup

  1. stirringthe reaction mixture was stirred for about 48 h at room temperature
  2. customThe solvent was removed under reduced pressure
  3. customthe crude material was purified by RP-HPLC (Table 2, Method q)

Sources & evidence

ORD record
ord-1300d4614f914c4a90fdd5c26c853b61
Source dataset
uspto-grants-2016_06
Patent number
US09365579B2

Reaction notes

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