Isopropyl chloroformate → HCID 11574991, compound

HRID 1362995Notes

Reaction equation

HRID 1362995 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[C:9]([NH2:22])[CH:10]=[CH:11][C:12]=2[O:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][S:19][CH2:18][CH2:17]2)=[CH:5][CH:4]=[N:3]1.C(Cl)Cl.N1C=CC=CC=1.Cl[C:33]([O:35][CH:36]([CH3:38])[CH3:37])=[O:34]>CS(C)=O>[CH:36]([O:35][C:33](=[O:34])[NH:22][C:9]1[CH:10]=[CH:11][C:12]([O:13][CH2:14][CH2:15][N:16]2[CH2:17][CH2:18][S:19][CH2:20][CH2:21]2)=[C:7]([C:6]2[N:2]([CH3:1])[N:3]=[CH:4][CH:5]=2)[CH:8]=1)([CH3:38])[CH3:37]

Participants

5

Reactant 3

HCID 7917Isopropyl chloroformateHCID 21875418Pyridine methylene chlorideHCID 58243077HCID 58243077, compound

Product 1

HCID 11574991HCID 11574991, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 3-(2-methyl-2H-pyrazol-3-yl)-4-(2-thiomorpholin-4-yl-ethoxy)-phenylamine (0.14 g, 0.443 mmol) in 2.0 mL/1.0 mL DCM/Pyridine mixture was added isopropyl chloroformate (0.06 g, 0.487 mmol), and the reaction mixture was stirred at room temperature overnight. The DCM/Pyridine mixture was evaporated to give a brown residue. The residue was dissolved in 5.0 mL of DMSO and was subjected to purification on RP-HPLC. The proper fractions were collected and lyophilized to produce [3-(2-Methyl-2H-pyrazol-3-yl)-4-(2-thiomorpholinyl-ethoxy)-phenyl]-carbamic acid isopropyl ester as a solid in 84% yield. LCMS m/z (%) 405 (M+H, 100). 1H NMR (400 MHz, Acetone-d6) δ: 8.58 (bs, 1H), 7.66 (dd, J=8.4 and 2.6 Hz, 1H), 7.55 (s, 1H), 7.47 (d, J=1.81 Hz, 1H), 7.28 (d, J=1.8 Hz, 1H), 7.16 (d, J=8.9 Hz, 1H), 6.05 (d, J=1.86 Hz, 1H), 4.92-4.98, (m, 1H), 4.53 (t, J=4.3 Hz, 2H), 3.72 (s, 3H), 3.59 (dd, J=9.63 and 4.86 Hz, 2H), 3.28-3.42 (m, 4H), 2.93-2.99 (m, 4H), 1.25 (d, J==6.12 Hz, 6M).

Workup

  1. customThe DCM/Pyridine mixture was evaporated
  2. customto give a brown residue
  3. customwas subjected to purification on RP-HPLC
  4. customThe proper fractions were collected

Sources & evidence

ORD record
ord-38b2397535e647309f842e35d0c202c8
Source dataset
uspto-grants-2011_02
Patent number
US07884101B2

Reaction notes

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