Triethylamine → HCID 22477186, compound

HRID 549016Notes

Reaction equation

HRID 549016 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([NH2:11])=[CH:8][CH:9]=2)[C:4]([C:12]2[NH:20][C:15]3=[N:16][CH:17]=[CH:18][CH:19]=[C:14]3[CH:13]=2)=[CH:3]1.C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>ClCCl>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([NH:11][S:29]([CH3:28])(=[O:31])=[O:30])=[CH:8][CH:9]=2)[C:4]([C:12]2[NH:20][C:15]3=[N:16][CH:17]=[CH:18][CH:19]=[C:14]3[CH:13]=2)=[CH:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22477390HCID 22477390, compound

Product 1

HCID 22477186HCID 22477186, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1-methyl-3-(1H-pyrrolo[2,3-b]pyridin-2-yl)-1H-indol-5-ylamine [52.4 mg, Example 18] in dichloromethane (5 mL) was treated with triethylamine (30 μl) followed by methane sulfonyl chloride (17 μl). After stirring at ambient temperature for 16 hours the reaction mixture was diluted with dichloromethane (10 mL), then washed with water (10 mL), then washed with brine (10 mL), then dried over magnesium sulfate and then evaporated. The residual solid was triturated with diethyl ether to give the title compound as a yellow solid, m.p. 223-224° C. MS: 341 (MH+).

Workup

  1. washwashed with water (10 mL)
  2. washwashed with brine (10 mL)
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residual solid was triturated with diethyl ether

Sources & evidence

ORD record
ord-61392ea11417472a9f59c00a6a044729
Source dataset
uspto-grants-2011_05
Patent number
US07943616B2

Reaction notes

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