Trifluoroacetic acid → 2-(7-chloro-thieno[3,2-b]pyridin-2-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2-(3-cyano-azetidin-1-yl)-1-cyclopropyl-2-oxo-ethyl]-amide

HRID 1898658Notes

Reaction equation

HRID 1898658 reaction equation
[C:1]([CH:3]1[CH2:6][N:5]([C:7](=[O:42])[C@H:8]([NH:12][C:13]([C:15]2[C:23]3[C:18](=[N:19][CH:20]=[C:21]([C:24]4[S:32][C:31]5[C:26](=[N:27][CH:28]=[CH:29][C:30]=5[Cl:33])[CH:25]=4)[N:22]=3)[N:17](COCC[Si](C)(C)C)[CH:16]=2)=[O:14])[CH:9]2[CH2:11][CH2:10]2)[CH2:4]1)#[N:2].FC(F)(F)C(O)=O>ClCCl>[C:1]([CH:3]1[CH2:4][N:5]([C:7](=[O:42])[C@H:8]([NH:12][C:13]([C:15]2[C:23]3[C:18](=[N:19][CH:20]=[C:21]([C:24]4[S:32][C:31]5[C:26](=[N:27][CH:28]=[CH:29][C:30]=5[Cl:33])[CH:25]=4)[N:22]=3)[NH:17][CH:16]=2)=[O:14])[CH:9]2[CH2:11][CH2:10]2)[CH2:6]1)#[N:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 584385872-(7-chloro-thieno[3,2-b]pyridin-2-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2-(3-cyano-azetidin-1-yl)-1-cyclopropyl-2-oxo-ethyl]-amide

Product 1

HCID 584386322-(7-chloro-thieno[3,2-b]pyridin-2-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2-(3-cyano-azetidin-1-yl)-1-cyclopropyl-2-oxo-ethyl]-amideYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(7-chloro-thieno[3,2-b]pyridin-2-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2-(3-cyano-azetidin-1-yl)-1-cyclopropyl-2-oxo-ethyl]-amide (30 mg, 0.048 mmol) in dichloromethane (2 mL) was added trifluoroacetic acid (0.37 mL, 4.82 mmol). The reaction mixture was stirred for 3 h at room temperature then concentrated and dried under high vacuum for 1 h. The residue was dissolved in 3 mL of CH2Cl2:MeOH:NH4OH (80:19:1) and stirred at room temperature for 18 h then evaporated to dryness under vacuum. The crude residue was washed with MeOH (3×3 mL) to give 17 mg (72%) of 2-(7-chloro-thieno[3,2-b]pyridin-2-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2-(3-cyano-azetidin-1-yl)-1-cyclopropyl-2-oxo-ethyl]-amide. MS: (M+H)+=492.

Workup

  1. concentrationthen concentrated
  2. customdried under high vacuum for 1 h
  3. dissolutionThe residue was dissolved in 3 mL of CH2Cl2:MeOH:NH4OH (80:19:1)
  4. stirringstirred at room temperature for 18 h
  5. customthen evaporated to dryness under vacuum
  6. washThe crude residue was washed with MeOH (3×3 mL)

Sources & evidence

ORD record
ord-a01edc819cfe4aa8b09ee59519de8bf3
Source dataset
uspto-grants-2013_08
Patent number
US08518945B2

Reaction notes

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