Methylamine → HCID 22676742, compound

HRID 1006265Notes

Reaction equation

HRID 1006265 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=1)[C:9]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:8]2[C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=1.[CH3:36][NH2:37]>O1CCCC1>[CH3:22][O:21][C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][CH:18]=1)[CH2:14][N:10]1[C:11]2[C:7](=[CH:6][C:5]([O:4][CH2:3][CH2:2][NH:37][CH3:36])=[CH:13][CH:12]=2)[C:8]([C:28]2[CH:29]=[CH:30][C:31]([O:34][CH3:35])=[CH:32][CH:33]=2)=[C:9]1[C:23]([O:25][CH2:26][CH3:27])=[O:24]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 22676782HCID 22676782, compound

Product 1

HCID 22676742HCID 22676742, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
120 °C

Procedure

A reaction mixture of ethyl 5-(2-chloroethoxy)-1-(3-methoxybenzyl)-3-(4-methoxyphenyl)-1H-indole-2-carboxylate (Example 152, 290 mg, 0.588 mmol) and methylamine in tetrahydrofuran (2 M, 40 ml) was sealed in a stainless steel vessel (100 ml, bomb) at 0° C. Then it was heated and stirred at 120° C. for 3 days in a oil bath. Oil bath was removed and the bomb was allowed to cooled to room temperature before opened. The reaction solution was transferred to an round-bottomed flask and solvent was concentrated in vacuo. The residue was dissolved in ethyl acetate and washed with 1N NaOH. The organic phase was dried over anhydrous sodium sulfate, concentrated and purified by flash column (silica gel, hexane: ethyl acetate=1:1 to ethyl acetate:2M NH3/ methanol =9:1). 214 mg desired product was obtained as a light yellow oil in 75%. MS (M+H)=489.2, Rf=0.28 (ethyl acetate:2M NH3/methanol=4:1).

Workup

  1. customwas sealed in a stainless steel vessel (100 ml, bomb) at 0° C
  2. temperatureThen it was heated
  3. customOil bath was removed
  4. temperatureto cooled to room temperature
  5. customThe reaction solution was transferred to an round-bottomed flask
  6. concentrationsolvent was concentrated in vacuo
  7. dissolutionThe residue was dissolved in ethyl acetate
  8. washwashed with 1N NaOH
  9. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  10. concentrationconcentrated
  11. custompurified by flash column (silica gel, hexane: ethyl acetate=1:1 to ethyl acetate:2M NH3/ methanol =9:1)

Sources & evidence

ORD record
ord-bb7a1bab0b9d4a44a543c6e2360b2df9
Source dataset
uspto-grants-2004_09
Patent number
US06787651B2

Reaction notes

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