Triethylamine → Methanesulfonic acid 5-[(5-bromo-imidazo[1,2-a]pyrazin-8-yl)-tert-butoxycarbonyl-amino]-2-morpholin-4-yl-benzyl ester

HRID 1925001Notes

Reaction equation

HRID 1925001 reaction equation
[C:1]([O:5][C:6](=[O:32])[N:7]([C:22]1[C:23]2[N:24]([CH:29]=[CH:30][N:31]=2)[C:25]([Br:28])=[CH:26][N:27]=1)[C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[C:10]([CH2:20][OH:21])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:40][S:41](Cl)(=[O:43])=[O:42]>C(Cl)Cl.C(OCC)(=O)C>[Br:28][C:25]1[N:24]2[CH:29]=[CH:30][N:31]=[C:23]2[C:22]([N:7]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:32])[C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)=[C:10]([CH:9]=2)[CH2:20][O:21][S:41]([CH3:40])(=[O:43])=[O:42])=[N:27][CH:26]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86652629(5-Bromo-imidazo[1,2-a]pyrazin-8-yl)-(3-hydroxymethyl-4-morpholin-4-yl-phenyl)-carbamic acid tert-butyl ester

Product 1

HCID 86652630Methanesulfonic acid 5-[(5-bromo-imidazo[1,2-a]pyrazin-8-yl)-tert-butoxycarbonyl-amino]-2-morpholin-4-yl-benzyl esterYield 113.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled solution (0° C.) of (5-bromo-imidazo[1,2-a]pyrazin-8-yl)-(3-hydroxymethyl-4-morpholin-4-yl-phenyl)-carbamic acid tert-butyl ester (0.17 g, 0.34 mmol) in DCM (0.5 mL), is added triethylamine (0.104 mL, 0.74 mmol) followed by methanesulfonyl chloride (0.046 mL, 0.6 mmol). The reaction mixture is stirred at 0° C. for 1 hour and an additional hour at room temperature. The reaction mixture is diluted with ethyl acetate and washed with water. The organic layer is dried over MgSO4, filtered and concentrated in vacuo to give the title compound (0.224 g) used in the next step without further purification.

Workup

  1. washwashed with water
  2. dry with materialThe organic layer is dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-36ef034299b24abea3c5ee573131ebf2
Source dataset
uspto-grants-2012_05
Patent number
US08178530B2

Reaction notes

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