Dichloromethane → HCID 57618513, compound

HRID 1690694Notes

Reaction equation

HRID 1690694 reaction equation
FC(F)(F)C(O)=O.[F:8][C:9]1[C:10]([C:27]2[CH:32]=[CH:31][C:30]([F:33])=[C:29]([CH3:34])[CH:28]=2)=[CH:11][CH:12]=[C:13]2[C:21]=1[NH:20][C:19]1[C:18]3[CH:22]=[CH:23][C:24]([NH2:26])=[CH:25][C:17]=3[CH2:16][CH2:15][C:14]2=1.ClCCl.[CH3:38][S:39](Cl)(=[O:41])=[O:40]>N1C=CC=CC=1>[F:8][C:9]1[C:10]([C:27]2[CH:32]=[CH:31][C:30]([F:33])=[C:29]([CH3:34])[CH:28]=2)=[CH:11][CH:12]=[C:13]2[C:21]=1[NH:20][C:19]1[C:18]3[CH:22]=[CH:23][C:24]([NH:26][S:39]([CH3:38])(=[O:41])=[O:40])=[CH:25][C:17]=3[CH2:16][CH2:15][C:14]2=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 31297Methanesulfonyl chlorideHCID 66904868HCID 66904868, compound

Product 1

HCID 57618513HCID 57618513, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A sample of 10-Fluoro-9-(4-fluoro-3-methyl-phenyl)-5,11-dihydro-6H-benzo[a]carbazol-3-ylamine trifluoroacetate (example 90) (17.8 mg, 0.038 mmol) is treated with dichloromethane (1 mL) and pyridine (0.5 mL). The reaction is then treated with methanesulfonyl chloride (8.6 mg, 7.5 mmol) and the reaction is stirred overnight at room temperature. The reaction is then concentrated and purified by reverse phase mass triggered HPLC to afford the title compound as a white solid after lyophilization: 1H NMR (400 MHz, d6-DMSO) δ 11.82 (s, 1H), 11.21 (s, 1H), 7.79 (d, J=8.2 Hz, 1H), 7.55 (m, 2H), 7.45 (m, 1M), 7.38 (m, 1H), 7.32 (d, J=8.1 Hz, 1H), 7.20 (m, 1H), 7.02 (dd, J=8.0, 7.0 Hz, 1H), 2.95 (m, 2H), 2.87 (m, 2H), 2.26 (s, 3H), 1.29 (s, 3H); LC/MS calculated for [M+H3O]+ C24H23F2N2O3S: 457.1, found: 457.0.

Workup

  1. concentrationThe reaction is then concentrated
  2. custompurified by reverse phase mass

Sources & evidence

ORD record
ord-44727a6e15e5445aa8d59625253c78a8
Source dataset
uspto-grants-2012_04
Patent number
US08153671B2

Reaction notes

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