Triethylamine → HCID 86613524, compound

HRID 1441326Notes

Reaction equation

HRID 1441326 reaction equation
[F:1][C:2]1[C:3]([C:20]2[N:24]([CH:25]([CH3:27])[CH3:26])[C:23]([CH3:28])=[N:22][CH:21]=2)=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:18][CH:17]([OH:19])[CH2:16]3)=[CH:11][CH:10]=2)=[N:6][CH:7]=1.C(N(CC)CC)C.[S:36](Cl)([CH3:39])(=[O:38])=[O:37]>C(Cl)Cl>[CH3:39][S:36]([O:19][CH:17]1[CH2:16][N:15]([C:12]2[CH:13]=[CH:14][C:9]([NH:8][C:5]3[N:4]=[C:3]([C:20]4[N:24]([CH:25]([CH3:26])[CH3:27])[C:23]([CH3:28])=[N:22][CH:21]=4)[C:2]([F:1])=[CH:7][N:6]=3)=[CH:10][CH:11]=2)[CH2:18]1)(=[O:38])=[O:37]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68689893HCID 68689893, compound

Product 1

HCID 86613524HCID 86613524, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To an ice cooled solution of 1-(4-{[5-fluoro-4-(1-isopropyl-2-methyl-1H-imidazol-5-yl)pyrimidin-2-yl]amino}phenyl)azetidin-3-ol (Example 137; 0.728 g, 1.905 mM) and triethylamine (153 μl, 2.09 mM) in dry DCM (22 ml), mesyl chloride (162 μl, 2.09 mM) was added. The reaction was stirred at 0° C. for 30 minutes and at room temperature for 20 hours. The reaction mixture was diluted with more DCM and extracted in turn with water (twice), saturated sodium chloride, dried with anhydrous sodium sulphate, filtered and evaporated to give the title compound as a brown foam (717 mg, 82%). NMR 1.37 (d, 6H), 2.48 (s, 3H+DMSO), 3.25 (s, 3H), 3.82 (m, 2H), 4.2 (m, 2H), 5.4 (m, 2H), 6.45 (d, 2H), 7.35 (m, 3H), 8.42 (d, 1H), 9.13 (s, 1H); m/z 461.

Workup

  1. extractionextracted in turn with water (twice), saturated sodium chloride
  2. dry with materialdried with anhydrous sodium sulphate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-b9fecc5da7bd4f22904d16717584690d
Source dataset
uspto-grants-2010_02
Patent number
US07655652B2

Reaction notes

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