Dimethylformamide → HCID 21985027, compound

HRID 1157892Notes

Reaction equation

HRID 1157892 reaction equation
FC(F)(F)C(O)=O.[NH:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[CH2:17][N:18]([CH2:29][C:30]1[CH:35]=[CH:34][C:33](N)=[CH:32][CH:31]=1)[CH:19]1[C:28]2[N:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH2:22][CH2:21][CH2:20]1.[N:37]1C=CC=CC=1S(Cl)(=O)=O.[CH3:47][N:48]([CH:50]=O)[CH3:49]>C(Cl)Cl>[NH:10]1[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N:8]=[C:9]1[CH2:17][N:18]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[N:37]=[CH:50][N:48]([CH3:49])[CH3:47])[CH:19]1[C:28]2[N:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH2:22][CH2:21][CH2:20]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6422Trifluoroacetic acidHCID 3787675Pyridine-2-sulfonyl ChlorideHCID 21985120HCID 21985120, compound

Product 1

HCID 21985027HCID 21985027, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1H-N-t-butoxycarbonyl-benzimidazol-2-ylmethyl)-[4-(t-butoxycarbonylamino)-benzyl]-(5,6,7,8-tetrahydroquinolin-8-yl)-amine (62 mg, 0.106 mmol) in CH2Cl2 (2 mL) was added trifluoroacetic acid (1 mL). The mixture was stirred at room temperature for 2 h, then concentrated. The residue was taken up in CH2Cl2, washed with 15% NaOH (3 mL) and extracted repeatedly with CH2Cl2. The combined organic fractions were dried over anhydrous sodium sulfate, filtered and concentrated. The crude (1H-benzimidazol-2-ylmethyl)-[4-aminobenzyl]-(5,6,7,8-tetrahydroquinolin-8-yl)-amine was then added to a solution of 2-pyridinesulfonyl chloride (27 mg, 0.15 mmol) in DMF (1 mL). The resulting solution was stirred at room temperature for 30 min. The mixture was then concentrated, taken up in CH2Cl2 and washed with aqueous potassium carbonate. The organic fraction was then dried over anhydrous sodium sulfate, filtered, concentrated and purified by chromatography on silica gel (10:1:0.1 CH2Cl2:MeOH:NH4OH) to afford N′-({[(1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydroquinolin-8-yl)-amino]-methyl}-phenyl)-N,N-dimethylformamidine (21 mg, 47%). 1H NMR (CDCl3) δ 1.69 (m, 1H), 2.01 (m, 3H), 2.25 (m, 1H), 2.73 (m, 2H), 2.93 (s, 3H), 3.60 (s, 3H), 3.62 (d, 1H, J=13.2 Hz), 3.68 (d, 1H, J=13.2 Hz), 3.98 (d, 1H, J=16.2 Hz), 4.01 (m, 1H), 4.12 (d, 1H, J=16.2 Hz), 6.80 (d, 2H, J=8.1 Hz), 7.16 (m, 4H), 7.26 (d, 1H, J=8.1 Hz), 7.38 (m, 2H), 7.40 (br s, 1H), 8.55 (d, 1H, J=4.8 Hz).

Workup

  1. concentrationconcentrated
  2. washwashed with 15% NaOH (3 mL)
  3. extractionextracted repeatedly with CH2Cl2
  4. dry with materialThe combined organic fractions were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. stirringThe resulting solution was stirred at room temperature for 30 min
  8. concentrationThe mixture was then concentrated
  9. washwashed with aqueous potassium carbonate
  10. dry with materialThe organic fraction was then dried over anhydrous sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated
  13. custompurified by chromatography on silica gel (10:1:0.1 CH2Cl2:MeOH:NH4OH)

Sources & evidence

ORD record
ord-d4d3557d3ce446ea8cf72f29bc0490ad
Source dataset
uspto-grants-2010_10
Patent number
US07807694B2

Reaction notes

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