Hydrochloric Acid → HCID 59833461, compound

HRID 269749Notes

Reaction equation

HRID 269749 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][N:10]([C:40]1[CH:45]=[C:44]([CH3:46])[CH:43]=[C:42]([CH3:47])[CH:41]=1)[CH2:11][C:12]1[CH:39]=[CH:38][C:15]2[N:16]=[C:17]([NH:28][CH2:29][CH2:30][CH2:31][N:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)[N:18]([CH2:19][C:20]3[C:25]([OH:26])=[CH:24][CH:23]=[C:22]([CH3:27])[N:21]=3)[C:14]=2[CH:13]=1)(C)(C)C.Cl>O.O1CCCC1>[NH2:7][CH2:8][CH2:9][N:10]([CH2:11][C:12]1[CH:39]=[CH:38][C:15]2[N:16]=[C:17]([NH:28][CH2:29][CH2:30][CH2:31][N:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)[N:18]([CH2:19][C:20]3[C:25]([OH:26])=[CH:24][CH:23]=[C:22]([CH3:27])[N:21]=3)[C:14]=2[CH:13]=1)[C:40]1[CH:41]=[C:42]([CH3:47])[CH:43]=[C:44]([CH3:46])[CH:45]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59833453HCID 59833453, compound

Product 1

HCID 59833461HCID 59833461, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (2-{(3,5-dimethyl-phenyl)-[3-(3-hydroxy-6-methyl-pyridin-2-ylmethyl)-2-(3-morpholin-4-yl-propylamino)-3H-benzoimidazol-5-ylmethyl]-amino}-ethyl)-carbamic acid tert-butyl ester, prepared as described for compounds n-4, (0.00012 mol) in a 3N solution of HCl in water (10 ml) and tetrahydrofuran (10 ml) was stirred at room temperature for 12 hours. The precipitate was filtered off and taken up in a 10% solution of K2CO3 in water. The solution was saturated with K2CO3 (powder) and extracted with CH2Cl2/CH3OH (95/5). The organic layer was separated, dried (over MgSO4), filtered and the solvent was evaporated until dryness. The residue (0.07 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 92/8/1; 10 μm). The pure fractions were collected and the solvent was evaporated. The residue was crystallized from CH3CN/CH3OH/diisopropylether, yielding 0.03 g of 2-[6-{[(2-amino-ethyl)-(3,5-dimethyl-phenyl)-amino]-methyl}-2-(3-morpholin-4-yl-propylamino)-benzoimidazol-1-ylmethyl]-6-methyl-pyridin-3-ol (Compound 66, 44%, melting point: 196° C.).

Workup

  1. customprepared
  2. filtrationThe precipitate was filtered off
  3. extractionextracted with CH2Cl2/CH3OH (95/5)
  4. customThe organic layer was separated
  5. dry with materialdried (over MgSO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated until dryness
  8. customThe residue (0.07 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 92/8/1; 10 μm)
  9. customThe pure fractions were collected
  10. customthe solvent was evaporated
  11. customThe residue was crystallized from CH3CN/CH3OH/diisopropylether

Sources & evidence

ORD record
ord-2bd5843ccfa44873a89d4af85fbc0f11
Source dataset
uspto-grants-2008_11
Patent number
US07449463B2

Reaction notes

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