Pyridine → HCID 57442270, compound

HRID 2079908Notes

Reaction equation

HRID 2079908 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:14]3[N:18]([CH2:19][CH3:20])[N:17]=[C:16]([C:21]#[N:22])[CH:15]=3)=[CH:7][N:8]2[CH:11]([CH3:13])[CH3:12])=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH3:29][S:30](Cl)(=[O:32])=[O:31]>C(Cl)Cl>[C:21]([C:16]1[CH:15]=[C:14]([C:6]2[C:5]3[C:9](=[CH:10][C:2]([NH:1][S:30]([CH3:29])(=[O:32])=[O:31])=[CH:3][CH:4]=3)[N:8]([CH:11]([CH3:12])[CH3:13])[CH:7]=2)[N:18]([CH2:19][CH3:20])[N:17]=1)#[N:22]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 57442269HCID 57442269, compound

Product 1

HCID 57442270HCID 57442270, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Stir a solution of 5-(6-Amino-1-isopropyl-1H-indol-3-yl)-1-ethyl-1H-pyrazole-3-carbonitrile (0.126 g, 0.393 mmol), pyridine (0.062 g, 0.786 mmol) and methanesulfonyl chloride (0.068 g, 0.590 mmol) in methylene chloride (3 mL) at room temperature for 2.5 h. After this time, Purify the reaction directly by chromatography (silica, methylene chloride to 1:9 ethyl acetate/methylene chloride) then freeze-dried from acetonitrile/water to afford N-[3-(5-Cyano-2-ethyl-2H-pyrazol-3-yl)-1-isopropyl-1H-indol-6-yl]-methanesulfonamide (0.132 g, 90%) as alight purple solid: mp 144-145° C.; 1H NMR (500 MHz, DMSO-d0.6 δ0.60 (s, 1H), 7.84 (s, 1H), 7.50 (d, J=9.0 Hz, 1H), 7.45 (d, J=2.0 Hz, 1H), 7.11 (s, 1H), 7.04 (dd, J=8.5, 1.5 Hz, 1H), 4.73 (m, 1H), 4.27 (q, J=7.0 Hz, 21H), 2.96 (s, 3H), 1.52 (d, J=6.5 Hz, 6H), 1.35 (t, J=7.0 Hz, 3H) LCMS (Method 4)>99%, 6.96 min, m/z 372 [M+H]+.

Workup

  1. customAfter this time, Purify
  2. customthe reaction directly by chromatography (silica, methylene chloride to 1:9 ethyl acetate/methylene chloride)
  3. dry with materialthen freeze-dried from acetonitrile/water

Sources & evidence

ORD record
ord-db7661d8d09546a9a9662f3cc82abb17
Source dataset
uspto-grants-2011_04
Patent number
US07932284B2

Reaction notes

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