Chlorotrimethylsilane → HCID 21465245, compound

HRID 1939936Notes

Reaction equation

HRID 1939936 reaction equation
C([O:4][C:5]([C:7]1[N:8]=[CH:9][C:10]2[NH:11][C:12]3[C:17]([C:18]=2[C:19]=1[CH2:20][O:21][CH3:22])=[CH:16][C:15]([O:23][C:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][N:25]=1)=[CH:14][CH:13]=3)=O)(C)C.C(N(CC)CC)C.Cl[Si](C)(C)C>C1(C)C=CC=CC=1>[C:24]1([O:23][C:15]2[CH:16]=[C:17]3[C:12](=[CH:13][CH:14]=2)[NH:11][C:10]2[CH:9]=[N:8][C:7]([CH:5]=[O:4])=[C:19]([CH2:20][O:21][CH3:22])[C:18]3=2)[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][N:25]=1

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 53706251HCID 53706251, compound

Product 1

HCID 21465245HCID 21465245, compoundYield 153.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-78 °C

Procedure

330 mg of 6-(1-isoquinolyloxy)-4-methoxymethyl-β-carboline-3-carboxylic acid isopropyl ester is mixed in 10 ml of toluene with 0.62 ml of triethylamine and 0.2 chlorotrimethylsilane and heated for 45 minutes to a bath temperature of 50°-60° C. After concentration by evaporation to about 6 ml, it is cooled to -78° C. under argon and 1.25 ml of a 1.2 molar diisobutyl aluminum hydride is instilled in hexane. After 30 minutes at -78° C., it is mixed with 3 ml of ethanol and 0.75 ml of 1N NaOH. It is mixed with ethyl acetate and very little water. The organic phase is separated and concentrated by evaporation without drying. The residue is mixed with hexane and yields 440 mg of 6-(1-isoquinolyloxy)-4-methoxymethyl-β-carboline-3-carbaldehyde. 254 mg of it is mixed in 2.5 ml of dimethylfuran with 67.5 mg of hydroxylamine hydrochloride and 69 mg of potassium hydroxide powder and allowed to stand for 16 hours at room temperature. The batch is poured on ice and the precipitate is suctioned off and rewashed with water. 133 mg of 6-(1-isoquinolyloxy-4-methoxymethyl-β-carboline-3-carbaldehyde oxime of melting point 215°-218° C. is obtained.

Workup

  1. temperatureheated for 45 minutes to a bath temperature of 50°-60° C
  2. concentrationAfter concentration
  3. customby evaporation to about 6 ml, it
  4. additionit is mixed with 3 ml of ethanol and 0.75 ml of 1N NaOH
  5. additionIt is mixed with ethyl acetate and very little water
  6. customThe organic phase is separated
  7. concentrationconcentrated by evaporation
  8. customwithout drying
  9. additionThe residue is mixed with hexane

Sources & evidence

ORD record
ord-589a0793e319487badae099084478a82
Source dataset
uspto-grants-1997_12
Patent number
US05698555

Reaction notes

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