Hydrochloric Acid → HCID 19788726, compound

HRID 1656599Notes

Reaction equation

HRID 1656599 reaction equation
[NH2:1][C:2]1[CH:29]=[CH:28][C:5]([O:6][CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][N:12]([C:15]([C:17]3[CH:22]=[CH:21][C:20]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])=[CH:19][CH:18]=3)=[O:16])[CH2:11][CH2:10]2)=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH3:36][S:37](Cl)(=[O:39])=[O:38].Cl>C(Cl)Cl>[CH3:36][S:37]([NH:1][C:2]1[CH:29]=[CH:28][C:5]([O:6][CH2:7][CH2:8][N:9]2[CH2:10][CH2:11][N:12]([C:15]([C:17]3[CH:22]=[CH:21][C:20]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])=[CH:19][CH:18]=3)=[O:16])[CH2:13][CH2:14]2)=[CH:4][CH:3]=1)(=[O:39])=[O:38]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 19788718HCID 19788718, compound

Product 1

HCID 19788726HCID 19788726, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the above amine (1.50 g, 3.59 mmol) in CH2Cl2 (30 mL) at 0° C. under nitrogen was added pyridine (0.58 mL, 7.18 mmol) and methanesulfonyl chloride (0.42 mL, 5.38 mmol). After stirring for 2 hours, the mixture was partitioned between 10% aqueous NaHCO3 and 4:1 CH2Cl2 /isopropanol. The organic phase was dried and concentrated to afford a residue which was treated with ethanolic HCl to give 0.85 g (48%) of the title compound as a hydrochloride: mp: 170°-175° C.; 1H NMR (DMSO-d6): δ 10.12 (s, 1H), 9.45 (s, 1H), 7.45 (d, J=8.56 Hz, 2H), 7.25 (d, J=8.59 Hz, 2H), 7.16 (d, J=8.96 Hz, 2H), 6.97 (d, J=8.97 Hz, 2H), 4.37 (m, 2H), 3.60-3.25 (m, 10H), 3.05 (s, 3H), 2.87 (s, 3H); IR (KBr): 3010, 2580, 2460, 1640, 1610 cm-1 ; MS (m/z) 497 (MH+, 10%), 198 (35), 79 (100).

Workup

  1. customthe mixture was partitioned between 10% aqueous NaHCO3 and 4:1 CH2Cl2 /isopropanol
  2. customThe organic phase was dried
  3. concentrationconcentrated
  4. customto afford a residue which

Sources & evidence

ORD record
ord-ce3b4694e3574194ac551f77ac9385b9
Source dataset
uspto-grants-1993_10
Patent number
US05254689

Reaction notes

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