HCID 67045406, compound → HCID 67045159, compound

HRID 1923922Notes

Reaction equation

HRID 1923922 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-f6613dfe574d471b9881f716052800bb
Source dataset
uspto-grants-2012_05
Patent number
US08178131B2

Reaction notes

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