Sodium Hydroxide → HCID 58557971, compound

HRID 1969632Notes

Reaction equation

HRID 1969632 reaction equation
[CH:1]1([S:4]([NH:7][C@@H:8]2[CH2:12][N:11]([C:13]([NH:15][CH2:16][C:17]3[N:18]=[C:19]4[CH:25]=[CH:24][N:23]([S:26]([C:29]5[CH:35]=[CH:34][C:32]([CH3:33])=[CH:31][CH:30]=5)(=[O:28])=[O:27])[C:20]4=[N:21][CH:22]=3)=O)[C@H:10]([CH3:36])[CH2:9]2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.O=P(Cl)(Cl)Cl.[OH-].[Na+]>>[CH3:36][C@H:10]1[N:11]([C:13]2[N:18]3[C:19]4[CH:25]=[CH:24][N:23]([S:26]([C:29]5[CH:35]=[CH:34][C:32]([CH3:33])=[CH:31][CH:30]=5)(=[O:28])=[O:27])[C:20]=4[N:21]=[CH:22][C:17]3=[CH:16][N:15]=2)[CH2:12][C@@H:8]([NH:7][S:4]([CH:1]2[CH2:3][CH2:2]2)(=[O:6])=[O:5])[CH2:9]1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 58557681HCID 58557681, compound

Product 1

HCID 58557971HCID 58557971, compoundYield 94%

Conditions

Temperature
60 °C

Procedure

A flask was charged with (2R,4S)-4-(cyclopropanesulfonamido)-2-methyl-N-((5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)methyl)pyrrolidine-1-carboxamide (0.11 g, 0.207 mmol, prepared using E from Preparation #14 and J from Example #5 Step C and CDI) and POCl3 (1.9 mL, 21 mmol). The reaction mixture was heated to about 60° C. resulting in a homogeneous mixture. After about 2 h, the reaction mixture was cooled to ambient temperature and crushed ice was added. After the ice had melted, 2 N aqueous NaOH was added until a pH of about 7 was obtained. The resulting precipitate was collected by filtration and dried in vacuo to provide N-((3S,5R)-5-methyl-1-(6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)pyrrolidin-3-yl)cyclopropane-sulfonamide (0.10 g, 94%) as a tan solid: LC/MS (Table 1, Method a) Rt=2.14 min; MS m/z: 515 (M+H)+.

Workup

  1. customresulting in a homogeneous mixture
  2. temperaturethe reaction mixture was cooled to ambient temperature
  3. customcrushed ice
  4. additionwas added
  5. customwas obtained
  6. filtrationThe resulting precipitate was collected by filtration
  7. customdried in vacuo

Sources & evidence

ORD record
ord-98e3409e50c940e4b250ed09f99637d6
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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