Methanesulfonyl chloride → HCID 58386076, compound

HRID 1963029Notes

Reaction equation

HRID 1963029 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[C:15]([CH2:16]O)=[CH:14][N:13]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)[N:12]=2)=[O:10])=[CH:4][CH:3]=1.CS([Cl:29])(=O)=O.CCN(C(C)C)C(C)C>C(Cl)Cl.O>[Br:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[C:15]([CH2:16][Cl:29])=[CH:14][N:13]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)[N:12]=2)=[O:10])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 58386141HCID 58386141, compound

Product 1

HCID 58386076HCID 58386076, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To mixture of N-(6-bromopyridin-3-yl)-1-(4-chlorophenyl)-4-(hydroxymethyl)-1H-pyrazole-3-carboxamide (330 mg, 0.810 mmol) in CH2Cl2 (15 mL) at RT was added methanesulfonyl chloride (0.101 mL, 1.295 mmol) and DIEA (0.283 mL, 1.619 mmol). The resulting mixture was stirred at room temperature over a weekend. The reaction mixture was diluted with H2O, stirred for 5 min and subjected to filtration. The solid collected was dried under vacuum to give Example 17D (340 mg, (99%) as a beige solid. 1H NMR (CDCl3) δ 4.98 (s, 2H), 7.44-7.53 (m, 2H), 7.61-7.72 (m. 2H), 8.06 (s, 1H), 8.20-8.28 (s, 2H), 8.53 (s, 1H), 8.79 (s, 1H). LCMS, [M+H]+=426.9.

Workup

  1. stirringstirred for 5 min
  2. filtrationsubjected to filtration
  3. customThe solid collected
  4. customwas dried under vacuum
  5. customto give Example 17D (340 mg, (99%) as a beige solid

Sources & evidence

ORD record
ord-4a77735ad74b49ad83da4b098e463234
Source dataset
uspto-grants-2013_04
Patent number
US08415386B2

Reaction notes

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