Methanol → 2-(4-(3-carbamoyl-4-(((3S,4S)-1-(5-cyanopyridin-2-yl)-4-methylpyrrolidin-3-yl)amino)pyrrolo[1,2-b]pyridazin-6-yl)-1H-pyrazol-1-yl)acetic acid

HRID 877769Notes

Reaction equation

HRID 877769 reaction equation
[C:1]([C:4]1[CH:9]=[N:8][N:7]2[CH:10]=[C:11]([C:13]3[CH:14]=[N:15][N:16]([CH2:18][C:19]([O:21]CC)=[O:20])[CH:17]=3)[CH:12]=[C:6]2[C:5]=1[NH:24][C@H:25]1[C@@H:29]([CH3:30])[CH2:28][N:27]([C:31]2[CH:36]=[CH:35][C:34]([C:37]#[N:38])=[CH:33][N:32]=2)[CH2:26]1)(=[O:3])[NH2:2].[OH-].[Na+].CO>O1CCCC1>[C:1]([C:4]1[CH:9]=[N:8][N:7]2[CH:10]=[C:11]([C:13]3[CH:14]=[N:15][N:16]([CH2:18][C:19]([OH:21])=[O:20])[CH:17]=3)[CH:12]=[C:6]2[C:5]=1[NH:24][C@H:25]1[C@@H:29]([CH3:30])[CH2:28][N:27]([C:31]2[CH:36]=[CH:35][C:34]([C:37]#[N:38])=[CH:33][N:32]=2)[CH2:26]1)(=[O:3])[NH2:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 68291422ethyl 2-(4-(3-carbamoyl-4-(((3S,4S)-1-(5-cyanopyridin-2-yl)-4-methylpyrrolidin-3-yl)amino)pyrrolo[1,2-b]pyridazin-6-yl)-1H-pyrazol-1-yl)acetate

Product 1

HCID 682916422-(4-(3-carbamoyl-4-(((3S,4S)-1-(5-cyanopyridin-2-yl)-4-methylpyrrolidin-3-yl)amino)pyrrolo[1,2-b]pyridazin-6-yl)-1H-pyrazol-1-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of the crude ethyl 2-(4-(3-carbamoyl-4-(((3S,4S)-1-(5-cyanopyridin-2-yl)-4-methylpyrrolidin-3-yl)amino)pyrrolo[1,2-b]pyridazin-6-yl)-1H-pyrazol-1-yl)acetate from Step 1, a 2 N aqueous solution of NaOH (0.5 mL), methanol (0.5 mL) and tetrahydrofuran (0.5 mL) was stirred at room temperature for 1 h. The organic solvents were evaporated in vacuo. The aqueous residue was treated with 1 N HCl (1 mL) and water (1 mL) and filtered. The filter cake was washed with water and dried under vacuum to give crude 2-(4-(3-carbamoyl-4-(((3S,4S)-1-(5-cyanopyridin-2-yl)-4-methylpyrrolidin-3-yl)amino)pyrrolo[1,2-b]pyridazin-6-yl)-1H-pyrazol-1-yl)acetic acid as dark brown solid (66.3 mg). This material was used in the next step without further purification. MS (ES+) m/z: 486.1 (M+H).

Workup

  1. customThe organic solvents were evaporated in vacuo
  2. additionThe aqueous residue was treated with 1 N HCl (1 mL) and water (1 mL)
  3. filtrationfiltered
  4. washThe filter cake was washed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-3e80fed6d9bf43a3a099cea7510b7b7d
Source dataset
uspto-grants-2015_03
Patent number
US08987268B2

Reaction notes

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