Hydrochloric Acid → HCID 68672253, compound

HRID 571903Notes

Reaction equation

HRID 571903 reaction equation
[NH2:1][C:2]1[CH:47]=[C:46]([N:48]2[CH2:53][CH2:52][N:51]([CH3:54])[CH2:50][CH2:49]2)[CH:45]=[CH:44][C:3]=1[C:4]([NH:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH2:16][C:17]3[CH:22]=[C:21]([F:23])[CH:20]=[C:19]([F:24])[CH:18]=3)[CH:14]=2)[N:9](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[N:8]=1)=[O:5].[CH3:55][S:56]([Cl:59])(=[O:58])=[O:57].Cl>ClCCl.N1C=CC=CC=1.O1CCOCC1>[ClH:59].[F:23][C:21]1[CH:22]=[C:17]([CH:18]=[C:19]([F:24])[CH:20]=1)[CH2:16][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[C:7]2[NH:6][C:4](=[O:5])[C:3]1[CH:44]=[CH:45][C:46]([N:48]2[CH2:53][CH2:52][N:51]([CH3:54])[CH2:50][CH2:49]2)=[CH:47][C:2]=1[NH:1][S:56]([CH3:55])(=[O:58])=[O:57]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chlorideHCID 68671304HCID 68671304, compound

Product 1

HCID 68672253HCID 68672253, compoundYield 63%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 2-amino-N-[5-(3,5-difluoro-benzyl)-1-trityl-1H-indazol-3-yl]-4-(4-methyl-piperazin-1-yl)-benzamide (29 mg, 0.04 mmol) in anhydrous dichloromethane (2 mL) and dry pyridine (0.05 mL), methanesulfonyl chloride (14.7 mg, 0.01 mL, 0.13 mmol) was added and the reaction mixture was stirred at room temperature for 8 hours. The mixture was poured into ice and was extracted with dichloromethane. The organic layer was washed with 0.1N HCl, then with water, dried over anhydrous Na2SO4 and concentrated to yield a crude whitish solid that was suspended in dioxane (1 mL). After adding 4M HCl in dioxane (0.1 mL) the suspension was stirred overnight. After concentration the residue was suspended in diethyl ether/MeOH 1:1, stirred for 20 min., filtered, washed with the same solvent mixture and dried. The desired product was obtained as the hydrochloride (15 mg, 0.025 mmol, 63%).

Workup

  1. additionThe mixture was poured into ice
  2. extractionwas extracted with dichloromethane
  3. washThe organic layer was washed with 0.1N HCl
  4. dry with materialwith water, dried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customto yield a crude whitish solid
  7. stirringwas stirred overnight
  8. concentrationAfter concentration the residue
  9. stirringstirred for 20 min.
  10. filtrationfiltered
  11. washwashed with the same solvent mixture
  12. customdried

Sources & evidence

ORD record
ord-b2e324f208854109b7288a8bb9cb48e2
Source dataset
uspto-grants-2015_05
Patent number
US09029356B2

Reaction notes

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