Hydrochloric Acid → 6-Cyclopropyl-3-(pyrimidin-5-ylamino)-pyrazine-2-carboxylic acid [1-methyl-5-(pyrrolidin-3-ylcarbamoyl)-1H-pyrazol-4-yl]-amide

HRID 2368371Notes

Reaction equation

HRID 2368371 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH:10]([NH:13][C:14]([C:16]2[N:17]([CH3:40])[N:18]=[CH:19][C:20]=2[NH:21][C:22]([C:24]2[C:29]([NH:30][C:31]3[CH:32]=[N:33][CH:34]=[N:35][CH:36]=3)=[N:28][CH:27]=[C:26]([CH:37]3[CH2:39][CH2:38]3)[N:25]=2)=[O:23])=[O:15])[CH2:9]1)=O)(C)(C)C.Cl>O1CCOCC1>[CH3:40][N:17]1[C:16]([C:14](=[O:15])[NH:13][CH:10]2[CH2:11][CH2:12][NH:8][CH2:9]2)=[C:20]([NH:21][C:22]([C:24]2[C:29]([NH:30][C:31]3[CH:36]=[N:35][CH:34]=[N:33][CH:32]=3)=[N:28][CH:27]=[C:26]([CH:37]3[CH2:39][CH2:38]3)[N:25]=2)=[O:23])[CH:19]=[N:18]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 547618213-[(4-{[6-Cyclopropyl-3-(pyrimidin-5-ylamino)-pyrazine-2-carbonyl]-amino}-2-methyl-2H-pyrazole-3-carbonyl)-amino]-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 547594556-Cyclopropyl-3-(pyrimidin-5-ylamino)-pyrazine-2-carboxylic acid [1-methyl-5-(pyrrolidin-3-ylcarbamoyl)-1H-pyrazol-4-yl]-amideYield 80.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 3-[(4-{[6-cyclopropyl-3-(pyrimidin-5-ylamino)-pyrazine-2-carbonyl]-amino}-2-methyl-2H-pyrazole-3-carbonyl)-amino]-pyrrolidine-1-carboxylic acid tert-butyl ester (38 mg, 69 μmol; example 236) in 1,4-dioxane (0.38 ml) was treated with HCl in dioxane (4M; 380 μl, 1.5 mmol) and the reaction mixture was stirred at r.t. for 4 h. The precipitate was filtered off and dried to yield the product as yellow solid (25 mg, 75%).

Workup

  1. filtrationThe precipitate was filtered off
  2. customdried

Sources & evidence

ORD record
ord-9ffd2b1a99864609881ba6992c3ed98f
Source dataset
uspto-grants-2014_04
Patent number
US08703768B2

Reaction notes

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