1-Hydroxybenzotriazole → HCID 59494589, compound

HRID 872013Notes

Reaction equation

HRID 872013 reaction equation
ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[Br:23][C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[N:29]([CH2:33][CH2:34][CH2:35][O:36][CH3:37])[CH:28]=[C:27]2[CH2:38][NH:39][CH:40]1[CH2:42][CH2:41]1.[C:43]([O:47][C:48]([N:50]1[CH2:55][CH2:54][O:53][C@@H:52]([C:56](O)=[O:57])[CH2:51]1)=[O:49])([CH3:46])([CH3:45])[CH3:44]>CN(C)C=O.C(OCC)(=O)C>[Br:23][C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[N:29]([CH2:33][CH2:34][CH2:35][O:36][CH3:37])[CH:28]=[C:27]2[CH2:38][N:39]([CH:40]1[CH2:42][CH2:41]1)[C:56]([C@@H:52]1[O:53][CH2:54][CH2:55][N:50]([C:48]([O:47][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:49])[CH2:51]1)=[O:57]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 6559076(2R)-4-((tert-butoxy)carbonyl)morpholine-2-carboxylic acidHCID 59494618HCID 59494618, compound

Product 1

HCID 59494589HCID 59494589, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-Hydroxybenzotriazole (162 mg) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (288 mg) were added successively to a solution of N-{[5-bromo-1-(3-methoxypropyl)indol-3-yl]methyl}cyclopropanamine (a compound of Reference Example 127(2), 405 mg) and (2R)-4-(tert-butoxycarbonyl)morpholin-2-carboxylic acid (231 mg) in N,N-dimethylformamide (12.5 ml) and the mixture was stirred at room temperature overnight. The mixture was diluted with ethyl acetate, washed with water, a saturated aqueous solution of sodium bicarbonate and saturated brine successively and dried over magnesium sulfate. The solvent was evaporated in vacuo and the resulted residue was purified with a silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=50/50 to 10/90) to give tert-butyl(2R)-2-{[{[5-bromo-1-(3-methoxypropyl)indol-3-yl]methyl}(cyclopropyl)amino]carbonyl}morpholin-4-carboxylate (581 mg) as a colorless oil.

Workup

  1. washwashed with water
  2. dry with materiala saturated aqueous solution of sodium bicarbonate and saturated brine successively and dried over magnesium sulfate
  3. customThe solvent was evaporated in vacuo
  4. customthe resulted residue was purified with a silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=50/50 to 10/90)

Sources & evidence

ORD record
ord-7e7ee89ad67a4ef5bfed74e3bbe46a9e
Source dataset
uspto-grants-2015_03
Patent number
US08975252B2

Reaction notes

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