4-Toluenesulfonyl chloride → HCID 89717979, compound

HRID 930195Notes

Reaction equation

HRID 930195 reaction equation
[S:1](Cl)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[N:12]1([CH2:18][CH2:19][CH2:20][NH:21][C:22]2[C:34]3[C:33]4[C:28](=[CH:29][C:30]([C:35]([O:37][CH3:38])=[O:36])=[CH:31][CH:32]=4)[NH:27][C:26]=3[N:25]=[C:24]([CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[C:42]([C:46](=[N:51][OH:52])[C:47]([F:50])([F:49])[F:48])[CH:41]=3)[N:23]=2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.C(Cl)Cl>[N:12]1([CH2:18][CH2:19][CH2:20][NH:21][C:22]2[C:34]3[C:33]4[C:28](=[CH:29][C:30]([C:35]([O:37][CH3:38])=[O:36])=[CH:31][CH:32]=4)[NH:27][C:26]=3[N:25]=[C:24]([CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[C:42]([C:46](=[N:51][O:52][S:1]([C:4]4[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=4)(=[O:3])=[O:2])[C:47]([F:50])([F:48])[F:49])[CH:41]=3)[N:23]=2)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 89717373HCID 89717373, compound

Product 1

HCID 89717979HCID 89717979, compoundYield 113.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Tosyl chloride (0.048 g, 0.251 mmol) was added portionwise to a cold mixture of methyl 4-((3-(piperidin-1-yl)propyl)amino)-2-(3-(2,2,2-trifluoro-1-(hydroxyimino)ethyl)benzyl)-9H-pyrimido[4,5-b]indole-7-carboxylate (0.130 g, 0.229 mmol), 4-dimethylaminopyridine (2.79 mg, 0.023 mmol) and triethylamine (0.038 mL, 0.274 mmol) in DCM (10.00 mL) to give a white suspension. After one hour at room temperature, the amber solution was diluted with DCM (10 mL) and washed with water (3×10 mL). The organic layer was dried over anh. MgSO4, filtered and concentrated to dryness to give methyl 4-((3-(piperidin-1-yl)propyl)amino)-2-(3-(2,2,2-trifluoro-1-((tosyloxy)imino)ethyl)benzyl)-9H-pyrimido[4,5-b]indole-7-carboxylate (188 mg, 99% yield) as a tan foam: MS m/z 723.2 (M+H)+; HPLC >89%, RT=2.09 minutes.

Workup

  1. customto give a white suspension
  2. washwashed with water (3×10 mL)
  3. dry with materialThe organic layer was dried over anh. MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-089224e27ae047989c535e99561b10cc
Source dataset
uspto-grants-2016_03
Patent number
US09296744B2

Reaction notes

Loading…