Hydrochloric Acid → HCID 67045308, compound

HRID 875706Notes

Reaction equation

HRID 875706 reaction equation
[Br: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]([CH: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.[ClH:33]>C(O)(C(F)(F)F)=O.C(Cl)Cl.CCOCC>[ClH:33].[NH2:25][C@@H:21]1[CH2:22][CH2:23][CH2:24][N:19]([C:3]2[C:2]([Br:1])=[CH:7][N:6]=[C:5]3[NH:8][CH:9]=[C:10]([NH:11][C:12]([CH:14]4[CH2:15][CH2:16][CH2:17][CH2:18]4)=[O:13])[C:4]=23)[CH2:20]1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 67045421HCID 67045421, compound

Product 1

HCID 67045308HCID 67045308, compoundYield 62%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of (R)-tert-butyl 1-(5-bromo-3-(cyclopentanecarboxamido)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperidin-3-ylcarbamate (65 mg, 0.13 mmol) in neat TFA (5 mL) was stirred at room temperature for 20 minutes. TFA was then removed in vacuo, and the residue was evaporated from CH2Cl2 (10 mL). The oily residue obtained was dissolved in CH2Cl2 (0.5 mL) and treated with 2M HCl in Et2O. After 30 minutes at room temperature, the solid formed was filtered, washed with additional Et2O and dried to provide (R)—N-(4-(3-aminopiperidin-1-yl)-5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)cyclopentanecarboxamide hydrochloride (38 mg, 62% yield) as a solid. 1H NMR (400 MHz, (CD3)2SO) δ 11.79 (s, 1H), 9.31 (s, 1H), 8.27 (br s, 1H), 8.23 (s, 1H), 7.59 (br s, 1H), 3.46-3.41 (m, 2H), 3.34-3.27 (m, 2H), 3.11-3.04 (m, 1H), 2.88-2.80 (m, 1H), 2.17-2.11 (m, 1H), 1.94-1.85 (m, 3H), 1.79-1.74 (m, 2H), 1.72-1.65 (m, 3H), 1.60-1.55 (m, 2H), 1.52-1.45 (m, 1H); LCMS (APCI+) m/z 406.0, 408.1 (M+H)+, Retention time=2.42 minutes (Method 2).

Workup

  1. customTFA was then removed in vacuo
  2. customthe residue was evaporated from CH2Cl2 (10 mL)
  3. customThe oily residue obtained
  4. customthe solid formed
  5. filtrationwas filtered
  6. washwashed with additional Et2O
  7. customdried

Sources & evidence

ORD record
ord-96b4fea0aa564a1d8f61b6f5dc08db2d
Source dataset
uspto-grants-2015_03
Patent number
US08981085B2

Reaction notes

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