Diisopropylethylamine → HCID 178510059, compound

HRID 1854507Notes

Reaction equation

HRID 1854507 reaction equation
[C:1]1([C@@H:13]2[CH2:17][CH2:16][CH:15]([NH2:18])[CH2:14]2)[C:5]2=[C:6]3[CH:12]=[CH:11][NH:10][C:7]3=[N:8][CH:9]=[C:4]2[NH:3][N:2]=1.Cl[C:20]1[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][N:21]=1.CCN(C(C)C)C(C)C>CCO>[C:1]1([C@@H:13]2[CH2:17][CH2:16][C@@H:15]([NH:18][C:20]3[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][N:21]=3)[CH2:14]2)[C:5]2=[C:6]3[CH:12]=[CH:11][NH:10][C:7]3=[N:8][CH:9]=[C:4]2[NH:3][N:2]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 51520946-Chloro-3-pyridinecarbonitrileHCID 178507671HCID 178507671, compound

Product 1

HCID 178510059HCID 178510059, compoundYield 4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(3R)-3-(3,6-Dihydropyrazolo[4,3-d]pyrrolo[2,3-b]pyridin-1-yl)cyclopentanamine (0.12 g, 0.48 mmol, Preparation #29), 6-chloronicotinonitrile (0.069 g, 0.48 mmol), and DIEA (0.13 mL, 0.75 mmol) were heated in EtOH (3.0 mL) at about 80° C. for about 10 h. The solvent was removed under reduced pressure and the crude material was purified by RP-HPLC (Table 2, Method h) to give 6-((1R,3R)-3-(3,6-dihydropyrazolo[4,3-d]pyrrolo[2,3-b]pyridin-1-yl)cyclopentylamino)nicotinonitrile (0.007, 4%): LC/MS (Table 2, Method a) Rt=1.86 min; m/z: 344 (M+H)+ and 6-((1R,3S)-3-(3,6-dihydropyrazolo[4,3-d]pyrrolo[2,3-b]pyridin-1-yl)cyclopentylamino)nicotinonitrile (0.009 g, 5%): LC/MS (Table 2, Method a) Rt=1.89 min; m/z: 344 (M+H)+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe crude material was purified by RP-HPLC (Table 2, Method h)

Sources & evidence

ORD record
ord-7d94992439e54aa6b89b33a5ecee0a25
Source dataset
uspto-grants-2015_02
Patent number
US08962629B2

Reaction notes

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