Hydrochloric Acid → HCID 58459131, compound

HRID 2036606Notes

Reaction equation

HRID 2036606 reaction equation
C(OC([NH:8][C@@H:9]([CH3:27])[C:10]([NH:12][C:13]1[C:14]([NH:23][CH:24]2[CH2:26][CH2:25]2)=[C:15]([CH:20]=[CH:21][CH:22]=1)[C:16]([O:18][CH3:19])=[O:17])=O)=O)(C)(C)C.Cl>CC(O)=O.O1CCOCC1>[NH2:8][C@H:9]([C:10]1[N:23]([CH:24]2[CH2:26][CH2:25]2)[C:14]2[C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:20][CH:21]=[CH:22][C:13]=2[N:12]=1)[CH3:27]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58459194HCID 58459194, compound

Product 1

HCID 58459131HCID 58459131, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A stirred solution of (S)-methyl 3-(2-(tert-butoxycarbonylamino)propanamido)-2-(cyclopropylamino)benzoate (600 mg, 1.6 mmol) in HOAc (20 mL) was heated at 60° C. for 1.5 h, and cooled to rt. After concentration of the mixture in vacuo, the residue was subjected to 4M HCl in dioxane (10 mL), and stirred at rt for 40 min. The mixture was concentrated in vacuo, dissolved in water (5 mL) and basified with 1N NaOH to pH 9.5. The mixture was concentrated and MeOH-DCM (1:1) was added to the residue to get the desired product into solution. The solution was concentrated in vacuo and the residue was purified by column chromatography on a silica gel column using DCM-MeOH—NH4OH (9:1:0.05) as eluent to give (S)-methyl 2-(1-aminoethyl)-1-cyclopropyl-1H-benzo[d]imidazole-7-carboxylate: 1H NMR (400 MHz, CDCl3) δ 7.86 (1H, d, J=8.0 Hz), 7.63 (1H, d, J=8.0 Hz), 7.27 (1H, t, J=8.0 Hz), 4.62 (1H, q, J=8.0 Hz), 4.01 (3H, s), 3.58-3.50 (3H, m), 1.65 (3H, d, J=8.0 Hz), 1.22-1.06 (2H, m), 0.95-0.65 (2H, m); LC-MS (ESI) m/z 260.0 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutiondissolved in water (5 mL)
  3. concentrationThe mixture was concentrated
  4. additionMeOH-DCM (1:1) was added to the residue

Sources & evidence

ORD record
ord-614606bf932b48f4969f0ab8b1be0430
Source dataset
uspto-grants-2013_11
Patent number
US08575183B2

Reaction notes

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