Hydrochloric Acid → 1657014-42-0

HRID 875703Notes

Reaction equation

HRID 875703 reaction equation
[Br:1][C:2]1[C:3]([N:17]2[CH2:22][CH2:21][CH2:20][C@@H:19]([NH:23]C(=O)OC(C)(C)C)[CH2:18]2)=[C:4]2[C:10]([NH:11][C:12]([CH:14]3[CH2:16][CH2:15]3)=[O:13])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[ClH:31]>C(O)(C(F)(F)F)=O.C(Cl)Cl.CCOCC>[ClH:31].[NH2:23][C@@H:19]1[CH2:20][CH2:21][CH2:22][N:17]([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]4)=[O:13])[C:4]=23)[CH2:18]1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 67045318HCID 67045318, compound

Product 1

HCID 670451631657014-42-0Yield 67%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

(R)-tert-Butyl 1-(5-bromo-3-(cyclopropanecarboxamido)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperidin-3-ylcarbamate (110 mg, 0.230 mmol) in TFA (5 mL) was stirred at room temperature for 30 minutes, and the TFA was removed in vacuo. The oily residue obtained was dissolved in CH2Cl2 (1 mL), and 2M HCl in Et2O was added. The mixture was stirred at ambient temperature for 30 minutes. The solid formed was filtered and triturated with CH3CN to provide (R)—N-(4-(3-aminopiperidin-1-yl)-5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)cyclopropanecarboxamide hydrochloride (70 mg, 67% yield). 1H NMR (400 MHz, (CD3)2SO) δ 11.82 (s, 1H), 9.65 (s, 1H), 8.26 (br s, 3H), 8.22 (s, 1H), 7.47 (s, 1H), 3.46-3.40 (m, 3H), 3.31-3.23 (m, 1H), 3.12-3.06 (m, 1H), 2.15-2.09 (m, 1H), 1.87-1.80 (m, 2H), 1.76-1.69 (m, 1H), 1.53-1.43 (m, 1H), 0.83-0.81 (m, 4H); LCMS (APCI+) m/z 378.8, 379.9 (M+H)+, Retention time=2.18 minutes (Method 2).

Workup

  1. customthe TFA was removed in vacuo
  2. customThe oily residue obtained
  3. customThe solid formed
  4. filtrationwas filtered
  5. customtriturated with CH3CN

Sources & evidence

ORD record
ord-e978635baa2d4d4685b3c626ce4bf1fa
Source dataset
uspto-grants-2015_03
Patent number
US08981085B2

Reaction notes

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