Trifluoroacetic acid → HCID 71555379, compound

HRID 706345Notes

Reaction equation

HRID 706345 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][NH:19][C:20]([NH:22][CH2:23][C:24]2[CH:29]=[CH:28][N:27]=[C:26]3[NH:30][CH:31]=[CH:32][C:25]=23)=[S:21])[CH:13]=1)=[O:10])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:30]1[C:26]2=[N:27][CH:28]=[CH:29][C:24]([CH2:23][NH:22][C:20](=[S:21])[NH:19][CH2:18][C:14]3[CH:13]=[C:12]([NH:11][C:9](=[O:10])[CH2:8][NH2:7])[CH:17]=[CH:16][CH:15]=3)=[C:25]2[CH:32]=[CH:31]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89535919HCID 89535919, compound

Product 1

HCID 71555379HCID 71555379, compoundYield 13.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 27-1 (100 mg, 0.32 mmol) and Boc-glycine (68 mg, 0.39 mmol) in DCM (10 mL) was added TEA (98 mg, 0.96 mmol) and HATU (184 mg, 0.48 mmol). the mixture was stirred at rt for 16 h. The mixture then washed with saturated sodium bicarbonate solution (aq), and the organic layer was dried and evaporated. The residue was purified by column chromatography to yield tert-butyl(2-((3-((3-((1H-pyrrolo[2,3-b]pyridin-4-yl)methyl)thioureido)methyl)phenyl)amino)-2-oxoethyl)carbamate (120 mg, 0.26 mmol). To a solution of tert-butyl(2-((3-((3-((1H-pyrrolo[2,3-b]pyridin-4-yl)methyl)thioureido)methyl)phenyl)amino)-2-oxoethyl)carbamate (120 mg, 0.26 mmol) in DCM (10 mL) was added TFA (2 mL). The mixture was stirred at rt for 0.5 h. Solvent was evaporated and the residue was purified by semi-prep HPLC to yield Example 112, N-(3-((3-((1H-pyrrolo[2,3-b]pyridin-4-yl)methyl)thioureido)methyl)phenyl)-2-aminoacetamide (13 mg).

Workup

  1. customSolvent was evaporated
  2. customthe residue was purified by semi-prep HPLC

Sources & evidence

ORD record
ord-6a70b336546f4853b2ee266526d43242
Source dataset
uspto-grants-2015_11
Patent number
US09174984B2

Reaction notes

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