Hydrochloric Acid → HCID 19828085, compound

HRID 1494428Notes

Reaction equation

HRID 1494428 reaction equation
[CH3:1][C:2]1[N:6]([C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[N:4][C:3]=1[CH:26]=O.[CH:28]([NH2:31])([CH3:30])[CH3:29].Cl.C([BH3-])#N.[Na+]>CO.O>[CH3:1][C:2]1[N:6]([C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[N:4][C:3]=1[CH2:26][NH:31][CH:28]([CH3:30])[CH3:29]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 6363IsopropylamineHCID 5003444Sodium cyanoborohydrideHCID 118243385-methyl-1-trityl-1H-imidazole-4-carbaldehyde

Product 1

HCID 19828085HCID 19828085, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 5-methyl-1-(triphenylmethyl)-1H-imidazole-4-carboxaldehyde (3.5 g) and isopropylamine (10 ml) in methanol (125 ml) was stirred at 20° for 1h. The resulting solution was treated with ethanolic hydrogen chloride (0.027 g/ml; 15 ml), cooled to 0° and treated with sodium cyanoborohydride (0.94 g). After stirring for 2.5 h, water (15 ml) was added and the resulting mixture was stirred at 20° for 0.5 h and treated with concentrated hydrochloric acid (6 ml). The mixture was warmed to 40°, stirred at 40° for 0.5h and concentrated in vacuo to ca. 50 ml. The concentrate was then basified (to pH9) with a saturated solution of potassium carbonate (200 ml) and extracted with ethyl acetate (3×100 ml). The organic extracts were combined, dried and evaporated to leave a gum (ca. 5 g) which was purified by FCC eluting with System A (100:8:1) to give the title compound (1.9 g) as a solid, m.p. 154°-156°. A second crop of product (0.4 g) has m.p. 150°-154°.

Workup

  1. temperaturecooled to 0°
  2. stirringAfter stirring for 2.5 h
  3. stirringthe resulting mixture was stirred at 20° for 0.5 h
  4. temperatureThe mixture was warmed to 40°
  5. concentrationconcentrated in vacuo to ca. 50 ml
  6. extractionextracted with ethyl acetate (3×100 ml)
  7. customdried
  8. customevaporated

Sources & evidence

ORD record
ord-af240057350a4f3e805a8669fcd4d8d0
Source dataset
uspto-grants-1991_06
Patent number
US05026722

Reaction notes

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