HCID 67045406, compound → HCID 67045159, compound

HRID 2203969Notes

Reaction equation

HRID 2203969 reaction equation
[Cl:1][C:2]1[C:3]([N:19]2[CH2:24][CH2:23][CH2:22][C@@H:21]([NH:25]C(=O)OC(C)(C)C)[CH2:20]2)=[C:4]2[C:10]([NH:11][C:12]([N:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)=[O:13])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1>C(O)(C(F)(F)F)=O>[ClH:1].[NH2:25][C@@H:21]1[CH2:22][CH2:23][CH2:24][N:19]([C:3]2[C:2]([Cl:1])=[CH:7][N:6]=[C:5]3[NH:8][CH:9]=[C:10]([NH:11][C:12]([N:14]4[CH2:18][CH2:17][CH2:16][CH2:15]4)=[O:13])[C:4]=23)[CH2:20]1

Participants

3

Reactant 1

HCID 67045406HCID 67045406, compound

Product 1

HCID 67045159HCID 67045159, compoundYield 199.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of (R)-tert-butyl 1-(5-chloro-3-(pyrrolidine-1-carboxamido)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperidin-3-ylcarbamate (130 mg, 0.281 mmol) in neat TFA (4 mL) was stirred at room temperature for 10 minutes, and then the TFA was removed in vacuo. The resulting oily residue was dissolved in CH3OH (5 mL) and evaporated from CH3CN (2×5 mL) to provide (R)—N-(4-(3-aminopiperidin-1-yl)-5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrrolidine-1-carboxamide hydrochloride (112 mg, 91% yield) as a solid. 1H NMR (400 MHz, (CD3)2SO) δ 1.68 (br s, 1H), 8.25 (s, 3H), 8.10 (s, 1H), 7.85 (s, 1H), 7.42 (d, 1H), 3.51-3.45 (m, 1H), 3.44-3.36 (m, 4H), 3.34-3.22 (m, 3H), 3.16-3.07 (m, 1H), 2.09-2.01 (m, 1H), 1.90-1.87 (m, 4H), 1.80-1.72 (m, 1H), 1.67-1.41 (m, 2H). LCMS (APCI+) m/z 363 (M+H)+.

Workup

  1. customthe TFA was removed in vacuo
  2. dissolutionThe resulting oily residue was dissolved in CH3OH (5 mL)
  3. customevaporated from CH3CN (2×5 mL)

Sources & evidence

ORD record
ord-93ed7a86694f43ac9974f33be8b80132
Source dataset
uspto-grants-2016_06
Patent number
US09365568B2

Reaction notes

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