4-Toluenesulfonyl chloride → HCID 89719318, compound

HRID 1480760Notes

Reaction equation

HRID 1480760 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].[C:12]([O:16][C:17]([NH:19][CH2:20][CH2:21][CH2:22][N:23]([CH3:59])[CH2:24][CH2:25][CH2:26][NH:27][C:28]1[C:40]2[C:39]3[C:34](=[CH:35][C:36]([C:41]([O:43][CH3:44])=[O:42])=[CH:37][CH:38]=3)[NH:33][C:32]=2[N:31]=[C:30]([CH2:45][C:46]2[CH:51]=[CH:50][CH:49]=[C:48]([C:52](=[N:57][OH:58])[C:53]([F:56])([F:55])[F:54])[CH:47]=2)[N:29]=1)=[O:18])([CH3:15])([CH3:14])[CH3:13].C(N(CC)CC)C>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:12]([O:16][C:17]([NH:19][CH2:20][CH2:21][CH2:22][N:23]([CH3:59])[CH2:24][CH2:25][CH2:26][NH:27][C:28]1[C:40]2[C:39]3[C:34](=[CH:35][C:36]([C:41]([O:43][CH3:44])=[O:42])=[CH:37][CH:38]=3)[NH:33][C:32]=2[N:31]=[C:30]([CH2:45][C:46]2[CH:51]=[CH:50][CH:49]=[C:48]([C:52](=[N:57][O:58][S:1]([C:4]3[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=3)(=[O:3])=[O:2])[C:53]([F:54])([F:56])[F:55])[CH:47]=2)[N:29]=1)=[O:18])([CH3:15])([CH3:14])[CH3:13]

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 89719310HCID 89719310, compound

Product 1

HCID 89719318HCID 89719318, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Ts-Cl (0.060 g, 0.315 mmol) was added portion-wise to a mixture of methyl 4-((3-((3-((tert-butoxycarbonyl)amino)propyl)(methyl)amino)propyl)amino)-2-(3-(2,2,2-trifluoro-1-(hydroxyimino)ethyl)benzyl)-9H-pyrimido[4,5-b]indole-7-carboxylate (0.184 g, 0.274 mmol), DMAP (3.35 mg, 0.027 mmol) and triethylamine (0.048 mL, 0.342 mmol) in DCM (12 mL) to give a tan solution. After 1 hour, the reaction mixture was diluted with DCM (12 mL), washed with water (3×12 mL) and the organic layer was dried over anh. MgSO4, filtered and concentrated to dryness to afford methyl 4-((3-((3-((tert-butoxycarbonyl)amino)propyl)(methyl)amino)propyl)amino)-2-(3-(2,2,2-trifluoro-1-((tosyloxy)imino)ethyl)benzyl)-9H-pyrimido[4,5-b]indole-7-carboxylate (217 mg, 96% yield) as a tan foam: MS m/z 826.2 (M+H)+; HPLC 93.2% @ 220 nm and 91.3% @ 254 nm, RT=2.20 minutes.

Workup

  1. customto give a tan solution
  2. washwashed with water (3×12 mL)
  3. dry with materialthe organic layer was dried over anh. MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-8a57d39c5031404eb59e6679b7853b83
Source dataset
uspto-grants-2016_08
Patent number
US09409906B2

Reaction notes

Loading…