Methanesulfonyl chloride → HCID 68464475, compound

HRID 501198Notes

Reaction equation

HRID 501198 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][C:8]([N:11]2[CH2:36][CH2:35][C:14]3[NH:15][C:16]4[CH:17]=[CH:18][C:19]([C:22]5[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][N:29]6[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]6)[CH:23]=5)=[CH:20][C:21]=4[C:13]=3[CH2:12]2)=[N:9][CH:10]=1)=[O:4].[CH3:37][S:38](Cl)(=[O:40])=[O:39]>C(Cl)Cl.CN(C)C1C=CN=CC=1.O>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][C:8]([N:11]2[CH2:36][CH2:35][C:14]3[NH:15][C:16]4[CH:17]=[CH:18][C:19]([C:22]5[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][N:29]6[CH2:30][CH2:31][N:32]([S:38]([CH3:37])(=[O:40])=[O:39])[CH2:33][CH2:34]6)[CH:23]=5)=[CH:20][C:21]=4[C:13]=3[CH2:12]2)=[N:9][CH:10]=1)=[O:4]

Participants

6

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 68464494HCID 68464494, compound

Product 1

HCID 68464475HCID 68464475, compoundYield 97.3%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of methyl-2-{8-[3-(piperazin-1-ylmethyl)phenyl]-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indol-2-yl}pyrimidine-5-carboxylate (800 mg, 1.65 mmol) in dry DCM (50 mL) was added 4-dimethylaminopyridine (1.012 g, 8.29 mmol), then methanesulfonyl chloride (0.155 mL, 1.99 mmol) was added at 0° C. and stirred for 10 min. The reaction mass was maintained at room temperature and stirred for 1 h. The progress of the reaction was monitored by TLC and after completion the reaction mass was diluted with water and extracted with DCM. The DCM layer dried over sodium sulfate and concentrated. The residue was purified by column chromatography to give methyl-2-{8-[3-((4-(methylsulfonyl)piperazin-1-yl)methyl)phenyl]-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indol-2-yl}pyrimidine-5-carboxylate (900 mg, 95.40%) with HPLC purity 95.40%. 1HNMR (200 MHz, CD3OD) δ: 2.62 (t, 4H, 2×CH2), 2.85 (s, 3H, CH3) 3.0 (t, 2H, CH2), 3.22 (t, 4H, 2×CH2), 3.7 (s, 2H, CH2) 3.95 (s, 3H, OCH3), 4.4 (t, 2H, CH2), 5.18 (s, 2H, CH2), 7.2-7.8 (m, 7H, Ar—H), 8.9 (s, 2H, Pyrimidine-H); m/e=561 (M+1).

Workup

  1. stirringstirred for 1 h
  2. extractionextracted with DCM
  3. dry with materialThe DCM layer dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-875ce6ed1139443087c6628b3c7654f2
Source dataset
uspto-grants-2010_08
Patent number
US07772245B2

Reaction notes

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