Isopropyl chloroformate → Isopropyl 4-({6-[5-(methylsulfonyl)indolin-1-yl]pyrimidin-4-yl}oxy)piperidine-1-carboxylate

HRID 448562

Reaction equation

HRID 448562 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([C:14]1[CH:19]=[C:18]([O:20][CH:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[N:17]=[CH:16][N:15]=1)[CH2:9][CH2:8]2)(=[O:4])=[O:3].C(N(CC)CC)C.Cl[C:35]([O:37][CH:38]([CH3:40])[CH3:39])=[O:36]>C(Cl)Cl>[CH:38]([O:37][C:35]([N:24]1[CH2:25][CH2:26][CH:21]([O:20][C:18]2[CH:19]=[C:14]([N:10]3[C:11]4[C:7](=[CH:6][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:13][CH:12]=4)[CH2:8][CH2:9]3)[N:15]=[CH:16][N:17]=2)[CH2:22][CH2:23]1)=[O:36])([CH3:40])[CH3:39]

Participants

5

Reactant 3

HCID 7917Isopropyl chloroformateHCID 8471TriethylamineHCID 667096685-(Methylsulfonyl)-1-(6-(piperidin-4-yloxy)pyrimidin-4-yl)indoline

Product 1

HCID 25260830Isopropyl 4-({6-[5-(methylsulfonyl)indolin-1-yl]pyrimidin-4-yl}oxy)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4b (0.12 mmol) and triethylamine (0.2 mL, 12 eq) in 1 mL of DCM, was added the isopropyl chloroformate (1.3 eq). The mixture was stirred at room temperature for 22 h and the solvent volume was reduced to 0.7 mL under a stream of nitrogen. The residue was purified by preparative HPLC to afford 4-1, LCMS 461.2 (MH+).

Workup

  1. customThe residue was purified by preparative HPLC
  2. customto afford 4-1, LCMS 461.2 (MH+)

Sources & evidence

ORD record
ord-f523c95db29e4f6bb646ad5b2e32ebe4
Source dataset
uspto-grants-2013_07
Patent number
US08481731B2

Linked notes

Loading…