Diisopropylethylamine → HCID 70837807, compound

HRID 448569Notes

Reaction equation

HRID 448569 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([C:16]2[CH:21]=[C:20]([N:22]3[C:30]4[C:25](=[CH:26][C:27]([S:31]([CH3:34])(=[O:33])=[O:32])=[CH:28][CH:29]=4)[CH2:24][CH2:23]3)[N:19]=[CH:18][N:17]=2)[CH3:15])[CH2:10][CH2:9]1)C1C=CC=CC=1.C(N(C(C)C)CC)(C)C.ClC(OC(Cl)C)=O>C(Cl)Cl>[CH3:34][S:31]([C:27]1[CH:26]=[C:25]2[C:30](=[CH:29][CH:28]=1)[N:22]([C:20]1[N:19]=[CH:18][N:17]=[C:16]([N:14]([CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)[CH3:15])[CH:21]=1)[CH2:23][CH2:24]2)(=[O:33])=[O:32]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5213051-Chloroethyl chloroformateHCID 86761923(1-Benzyl-piperidin-4-yl)-[6-(5-methanesulfonyl-2,3-dihydro-indol-1-yl)-pyrimidin-4-yl]-methyl-amine

Product 1

HCID 70837807HCID 70837807, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7c was taken up in DCM (2 mL). Diisopropylethylamine (0.6 mL, 11 eq) and 1-chloroethyl chloroformate (0.2 mL, 5.7 eq) were added. The reaction mixture was stirred at room temperature for 22 h. The solvent was then evaporated under a stream of nitrogen and the residue was dissolved in methanol and heated at 50° C. for 3 h. The solvent was removed under a stream of nitrogen and the residue was purified by preparative HPLC to give 25 mg (15%) of 7d.

Workup

  1. customThe solvent was then evaporated under a stream of nitrogen
  2. dissolutionthe residue was dissolved in methanol
  3. temperatureheated at 50° C. for 3 h
  4. customThe solvent was removed under a stream of nitrogen
  5. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-1fa52065bbc347d58b5b026088b5c88a
Source dataset
uspto-grants-2013_07
Patent number
US08481731B2

Reaction notes

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