Trifluoroacetic acid → HCID 49841659, compound

HRID 1627082Notes

Reaction equation

HRID 1627082 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([NH:15][CH2:16][C:17]2[C:25]3[C:24]([C:26](O)=[O:27])=[CH:23][CH:22]=[N:21][C:20]=3[NH:19][CH:18]=2)([CH3:14])[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:14][C:11]1([N:15]2[CH2:16][C:17]3=[CH:18][NH:19][C:20]4[C:25]3=[C:24]([CH:23]=[CH:22][N:21]=4)[C:26]2=[O:27])[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67224282HCID 67224282, compound

Product 1

HCID 49841659HCID 49841659, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The crude 3-((1-(tert-butoxycarbonyl)-4-methylpiperidin-4-ylamino)methyl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid obtained in Example 4 was dissolved in DCM (3 mL) and TFA (1 mL) and allowed to stir at room temperature for 1 h. The solution was concentrated in vacuo and purified via preparative HPLC 5% to 20% B in A and gave 21 mg of the title compound as its TFA salt. 1H NMR (400 MHz, CD3OD) δ 8.74 (s, 1H), 8.42 (m, 1H), 7.59 (m, 1H), 7.43 (m, 1H), 5.05 (s, 2H), 3.29-3.33 (m, 2H), 3.22-3.23 (m, 2H), 2.93-2.97 (m, 2H), 2.20-2.26 (m, 2H), 3.17 (s, 3H). [M+H] found 271.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. custompurified via preparative HPLC 5% to 20% B in A

Sources & evidence

ORD record
ord-ec2c33fd50fb4fc8937f3c80b5336c63
Source dataset
uspto-grants-2014_07
Patent number
US08785429B2

Reaction notes

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