Imidazole → HCID 70226972, compound

HRID 1531572Notes

Reaction equation

HRID 1531572 reaction equation
[C:1]([O:5][C:6](=[O:50])[N:7]([CH2:27][CH2:28][C:29]1[C:37]2[C:32](=[CH:33][CH:34]=C(NC(=O)C)C=2)[NH:31][C:30]=1[C:42]1[CH:47]=[C:46]([CH3:48])[CH:45]=[C:44]([CH3:49])[CH:43]=1)[CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[C:14]([S:19]([CH3:22])(=[O:21])=[O:20])[C:13]=1[S:23]([CH3:26])(=[O:25])=[O:24])([CH3:4])([CH3:3])[CH3:2].[C:51]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[NH:70]1[CH:74]=[CH:73][N:72]=[CH:71]1.[N:75](C(OCC)=O)=[N:76]C(OCC)=O>>[C:1]([O:5][C:6](=[O:50])[N:7]([CH2:27][CH2:28][C:29]1[C:37]2[C:32](=[CH:33][CH:34]=[C:74]([N:70]3[C:71]([CH3:51])=[N:72][N:76]=[N:75]3)[CH:73]=2)[NH:31][C:30]=1[C:42]1[CH:47]=[C:46]([CH3:48])[CH:45]=[C:44]([CH3:49])[CH:43]=1)[CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[C:14]([S:19]([CH3:22])(=[O:21])=[O:20])[C:13]=1[S:23]([CH3:26])(=[O:25])=[O:24])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 4

HCID 795Imidazole2×HCID 11776Triphenylphosphine2×HCID 220568ethyl N-ethoxycarbonyliminocarbamate2×HCID 70223405HCID 70223405, compound

Product 1

HCID 70226972HCID 70226972, compound

Procedure

To a solution of {2-[5-acetylamino-2-(3,5-dimethylphenyl)-1H-indol-3-yl]ethyl}-[4-(4-amino(dimethanesulfonyl)phenyl)butyl] carbamic acid tert-butyl ester (30 mg in 1.5 mL dry methylene chloride) was added in order 22.8 mg triphenylphosphine, 6.3 mg imidazole, 20.7 mg zinc azide(pyridine complex) and 0.014 mL diethyl azodicarboxylate and the mixture stirred at room temperature. After 4 hours additional portions of triphenylphosphine (11.3 mg), imidazole (3.5 mg), zinc azide•2 pyridine (11 mg) and diethyl azodicarboxylate (0.007 mL) were added and the mixture heated to reflux on an oil bath. After an additional 3 hours reaction time, the pot was cooled to room temperature and the reaction mixture applied directly to a silica gel column for purification by flash chromatography (hexane:ethyl acetate, 2:3) to give the title compound (26 mg).

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux on an oil bath
  3. customAfter an additional 3 hours reaction time
  4. temperaturethe pot was cooled to room temperature
  5. customthe reaction mixture applied directly to a silica gel column for purification by flash chromatography (hexane:ethyl acetate, 2:3)

Sources & evidence

ORD record
ord-a0a7efa81f3e43dabea047fc6bc3c694
Source dataset
uspto-grants-2001_03
Patent number
US06197975B1

Reaction notes

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