Hydrochloric Acid → (R)-(3-Aminopiperidin-1-yl)(2-(1-(cyclopropylmethyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)-1-methyl-1H-benzo[d]imidazol-5-yl)methanone, hydrochloride

HRID 2275040Notes

Reaction equation

HRID 2275040 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]([C:10]2[CH:32]=[CH:31][C:13]3[N:14]([CH3:30])[C:15]([C:17]4[N:25]([CH2:26][CH:27]5[CH2:29][CH2:28]5)[C:20]5=[N:21][CH:22]=[CH:23][CH:24]=[C:19]5[CH:18]=4)=[N:16][C:12]=3[CH:11]=2)=[O:9])[CH2:3]1.[ClH:33]>ClCCl.C(O)C>[ClH:33].[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]([C:10]2[CH:32]=[CH:31][C:13]3[N:14]([CH3:30])[C:15]([C:17]4[N:25]([CH2:26][CH:27]5[CH2:28][CH2:29]5)[C:20]5=[N:21][CH:22]=[CH:23][CH:24]=[C:19]5[CH:18]=4)=[N:16][C:12]=3[CH:11]=2)=[O:9])[CH2:3]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 72725333(R)-(3-Aminopiperidin-1-yl)(2-(1-(cyclopropylmethyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)-1-methyl-1H-benzo[d]imidazol-5-yl)methanone

Product 1

HCID 72725332(R)-(3-Aminopiperidin-1-yl)(2-(1-(cyclopropylmethyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)-1-methyl-1H-benzo[d]imidazol-5-yl)methanone, hydrochlorideYield 96.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-(3-aminopiperidin-1-yl)(2-(1-(cyclopropylmethyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)-1-methyl-1H-benzo[d]imidazol-5-yl)methanone (2.61 g, 6.09 mmol) in dichloromethane (DCM) (1.5 mL) was added HCl (2M in diethyl ether) (3 ml, 6.00 mmol). The mixture was sonicated for 2 minutes and then concentrated under vacuum to afford a yellow solid. This was dissolved in a minimum volume of hot ethanol. The solvent was removed under nitrogen and the product dried in a vacuum pistol at 50° C. overnight and then at 60° C. over the weekend to give the title compound as a yellow solid (2.7 g).

Workup

  1. customThe mixture was sonicated for 2 minutes
  2. concentrationconcentrated under vacuum
  3. customto afford a yellow solid
  4. customThe solvent was removed under nitrogen
  5. customthe product dried in a vacuum pistol at 50° C. overnight

Sources & evidence

ORD record
ord-0495c669643a4e0390440790cbce4d53
Source dataset
uspto-grants-2015_09
Patent number
US09127003B2

Reaction notes

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