Hydrochloric Acid → HCID 86689837, compound

HRID 2409023Notes

Reaction equation

HRID 2409023 reaction equation
C(O[C:6]([N:8]([CH2:10][C:11]1[N:16]=[C:15]2[CH:17]=[CH:18][N:19](C(OC(C)(C)C)=O)[C:14]2=[CH:13][CH:12]=1)C)=O)(C)(C)C.[ClH:27].O1CCOCC1>CO.C(Cl)Cl>[ClH:27].[CH3:6][NH:8][CH2:10][C:11]1[N:16]=[C:15]2[CH:17]=[CH:18][NH:19][C:14]2=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 86689835HCID 86689835, compound

Product 1

HCID 86689837HCID 86689837, compoundYield 96.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of tert-butyl 5-((tert-butoxycarbonyl(methyl)amino)-methyl)-1H-pyrrolo[3,2-b]pyridine-1-carboxylate (140.0 mg, 0.387 mmol) in MeOH (2 mL) and DCM (2 mL) was added HCl in dioxane (2.3 mL, 9.05 mmol, 4M) and the reaction mixture was stirred at 50° C. under N2 for 7 h. The solvent was removed in vacuo and the crude product was pumped dry on high-vacuum line to afford 87.1 mg (96.1%) of the desired product as HCl salt: 1H NMR (400 MHz, DMSO-d6) δ 12.51 (br s, 1H), 9.74 (br s, 2H), 8.38 (d, J=7.9 Hz, 1H), 8.10 (s, 1H), 7.68 (d, J=8.0 Hz, 1H), 6.78 (s, 1H), 4.52 (s, 2H), 2.63 (s, 3H); MS (ESI) m/z: 162.3 [M+1]+.

Workup

  1. customThe solvent was removed in vacuo
  2. dry with materialthe crude product was pumped dry on high-vacuum line

Sources & evidence

ORD record
ord-122e292470c94e41bfe9c191a7f98d95
Source dataset
uspto-grants-2014_08
Patent number
US08815877B2

Reaction notes

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