Isopropyl chloroformate → 4-[6-(5-Methanesulfonyl-2,3-dihydro-indol-1-yl)-pyrimidin-4-yl-methylamino]-piperidine-1-carboxylic acid isopropyl ester

HRID 448570Notes

Reaction equation

HRID 448570 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[N:19]=[CH:18][N:17]=[C:16]([N:20]([CH:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)[CH3:21])[CH:15]=1)[CH2:9][CH2:8]2)(=[O:4])=[O:3].C(N(CC)CC)C.Cl[C:36]([O:38][CH:39]([CH3:41])[CH3:40])=[O:37]>C(Cl)Cl.C1(C)C=CC=CC=1>[CH:39]([O:38][C:36]([N:25]1[CH2:26][CH2:27][CH:22]([N:20]([C:16]2[CH:15]=[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:19]=[CH:18][N:17]=2)[CH3:21])[CH2:23][CH2:24]1)=[O:37])([CH3:41])[CH3:40]

Participants

6

Reactant 3

HCID 7917Isopropyl chloroformateHCID 8471TriethylamineHCID 70837807HCID 70837807, compound

Product 1

HCID 498487864-[6-(5-Methanesulfonyl-2,3-dihydro-indol-1-yl)-pyrimidin-4-yl-methylamino]-piperidine-1-carboxylic acid isopropyl ester

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

7d was dissolved in DCM (1 mL) and triethylamine (0.1 mL, 14 eq) was added. Isopropyl chloroformate (0.1 mL of a 1 M solution in toluene, 2 eq) was added and the reaction mixture was stirred at room temperature for 17 h. The solution was evaporated and purified by preparative HPLC to give 7-1; LC-MS 474.0 (MH+), tR=5.21 (Method 5). EC50: 69 nM.

Workup

  1. customThe solution was evaporated
  2. custompurified by preparative HPLC
  3. customto give 7-1

Sources & evidence

ORD record
ord-ce45754b58744c7cbaa8041f9d4c722e
Source dataset
uspto-grants-2013_07
Patent number
US08481731B2

Reaction notes

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