N,N-Dimethyl-1,3-propanediamine → HCID 10050193, compound

HRID 1897477Notes

Reaction equation

HRID 1897477 reaction equation
[F:1][C:2]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:3]=1[O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[S:14](Cl)(=[O:16])=[O:15])[N:10]([CH2:18][CH:19]([CH3:21])[CH3:20])[N:9]=[CH:8]2.[CH3:27][N:28]([CH3:33])[CH2:29][CH2:30][CH2:31][NH2:32].C(N(CC)CC)C>ClCCl>[CH3:27][N:28]([CH3:33])[CH2:29][CH2:30][CH2:31][NH:32][S:14]([C:13]1[CH:12]=[C:11]2[C:7]([CH:8]=[N:9][N:10]2[CH2:18][CH:19]([CH3:21])[CH3:20])=[CH:6][C:5]=1[O:4][C:3]1[CH:22]=[CH:23][C:24]([F:26])=[CH:25][C:2]=1[F:1])(=[O:16])=[O:15]

Participants

5

Reactant 3

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 8471TriethylamineHCID 57418766HCID 57418766, compound

Product 1

HCID 10050193HCID 10050193, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cooled (0° C.) solution of 5-(2,4-difluorophenoxy)-1-isobutyl-1H-indazole-6-sulfonyl chloride (0.20 g, 0.50 mmol) in dichloromethane under N2 atmosphere was added 3-(dimethylamino)propylamine (0.05 g, 0.50 mmol) and triethylamine (0.15 g, 1.5 mmol) drop-wise. The reaction mixture was stirred for 4 hours and then diluted with dichloromethane (20 mL), washed with water, saturated NaHCO3 and brine and then dried over MgSO4. The mixture was concentrated under reduced pressure and chromatographed on preparatory TLC plates eluting with dichloromethane/MeOH/Et3N (95:4:1) to afford the 93 mg of final product (40% yield). MS (APCI−) m/z 466 detected; 1H NMR (400 mHz, CDCl3) δ 8.15 (s, 1H), 7.91 (s, 1H), 7.20 (m, 1H), 7.09 (s, 1H), 7.00 (m, 1H), 6.90 (m, 1H), 4.22 (d, 2H), 3.12 (t, 2H), 2.35 (m, 3H), 2.13 (s, 6H), 1.70 (m, 2H), 0.94 (d, 6H).

Workup

  1. washwashed with water, saturated NaHCO3 and brine
  2. dry with materialdried over MgSO4
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customchromatographed on preparatory TLC plates
  5. washeluting with dichloromethane/MeOH/Et3N (95:4:1)

Sources & evidence

ORD record
ord-e5d526051e084406a3dca96a0f77cd3c
Source dataset
uspto-grants-2013_08
Patent number
US08518983B2

Reaction notes

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