Methyl iodide → HCID 67420473, compound

HRID 1038076Notes

Reaction equation

HRID 1038076 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C:10]([C:15](=[O:54])[NH:16][C:17]2[CH:25]=[C:24]3[C:20]([C:21]([C:45]4[CH:50]=[CH:49][N:48]=[C:47]([CH:51]5[CH2:53][CH2:52]5)[CH:46]=4)=[N:22][N:23]3[C:26]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:19][CH:18]=2)([O:13][CH3:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:57]I>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C:10]([C:15](=[O:54])[N:16]([C:17]2[CH:25]=[C:24]3[C:20]([C:21]([C:45]4[CH:50]=[CH:49][N:48]=[C:47]([CH:51]5[CH2:52][CH2:53]5)[CH:46]=4)=[N:22][N:23]3[C:26]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[CH:19][CH:18]=2)[CH3:57])([O:13][CH3:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67419440HCID 67419440, compound

Product 1

HCID 67420473HCID 67420473, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-[3-(2-Cyclopropyl-pyridin-4-yl)-1-trityl-1H-indazol-6-ylcarbamoyl]-3-methoxy-pyrrolidine-1-carboxylic acid tert-butyl ester 3M (216 mg, 0.3 mmol) was dissolved in THF (10 mL) at r.t. To this solution was added NaH (40 mg, 60% suspension in mineral oil, 1 mmol). After stirring for 10 min, CH3I (0.6 mL, 9.6 mmol) was added. The reaction was worked up after 4 hrs by quenching with sat. NH4Cl solution. After extraction with ethyl acetate, the combined organic layers was dried and concentrated in vacuo to obtain 4M. 4M is used as the resulting crude.

Workup

  1. waitThe reaction was worked up after 4 hrs
  2. customby quenching with sat. NH4Cl solution
  3. extractionAfter extraction with ethyl acetate
  4. customthe combined organic layers was dried
  5. concentrationconcentrated in vacuo
  6. customto obtain 4M

Sources & evidence

ORD record
ord-c2b1b9980d034c048f324d3f7f355d38
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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