Triethylamine → 4-[6-(5-Methanesulfonyl-2,3-dihydro-indol-1-yl)-pyrimidin-4-yloxy]-piperidine-1-carboxylic acid cyclobutyl ester

HRID 448563Notes

Reaction equation

HRID 448563 reaction equation
C1(O)CCC1.C(N(CC)CC)C.Cl[C:14]([O:16][C:17]1[CH:22]=[CH:21][C:20]([N+]([O-])=O)=CC=1)=[O:15].[CH3:26][S:27]([C:30]1[CH:31]=[C:32]2[C:36](=[CH:37][CH:38]=1)[N:35]([C:39]1[CH:44]=[C:43]([O:45][CH:46]3[CH2:51][CH2:50][NH:49][CH2:48][CH2:47]3)[N:42]=[CH:41][N:40]=1)[CH2:34][CH2:33]2)(=[O:29])=[O:28]>C(Cl)Cl>[CH:17]1([O:16][C:14]([N:49]2[CH2:50][CH2:51][CH:46]([O:45][C:43]3[CH:44]=[C:39]([N:35]4[C:36]5[C:32](=[CH:31][C:30]([S:27]([CH3:26])(=[O:29])=[O:28])=[CH:38][CH:37]=5)[CH2:33][CH2:34]4)[N:40]=[CH:41][N:42]=3)[CH2:47][CH2:48]2)=[O:15])[CH2:22][CH2:21][CH2:20]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 76218CyclobutanolHCID 821294-Nitrophenyl chloroformateHCID 667096685-(Methylsulfonyl)-1-(6-(piperidin-4-yloxy)pyrimidin-4-yl)indoline

Product 1

HCID 252608324-[6-(5-Methanesulfonyl-2,3-dihydro-indol-1-yl)-pyrimidin-4-yloxy]-piperidine-1-carboxylic acid cyclobutyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the cyclobutanol (0.48 mmol, 4 eq) and triethylamine (0.3 mL, 4.4 eq) in 1 mL of DCM, was added 4-nitrophenyl chloroformate (0.1 g, 4.2 eq) and the mixture was stirred at room temp for 17 h. This solution was then added to a vial containing 4b (0.12 mmol) and the reaction mixture was stirred for 5 h at room temperature. The solvent volume was reduced to 0.7 mL under a stream of nitrogen and the residue was purified by preparative HPLC to afford 5-1, LCMS 473.4 (MH+).

Workup

  1. additionThis solution was then added to a vial
  2. stirringthe reaction mixture was stirred for 5 h at room temperature
  3. customthe residue was purified by preparative HPLC
  4. customto afford 5-1, LCMS 473.4 (MH+)

Sources & evidence

ORD record
ord-22bde8578bec4ea5a94aa40dab9e9785
Source dataset
uspto-grants-2013_07
Patent number
US08481731B2

Reaction notes

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