Methanesulfonamide → HCID 118235463, compound

HRID 626996Notes

Reaction equation

HRID 626996 reaction equation
[F:1][CH:2]([F:36])[O:3][C:4]1[CH:35]=[CH:34][CH:33]=[CH:32][C:5]=1[CH2:6][C:7]1[N:11]2[CH:12]=[C:13]([C:16]3[CH:17]=[N:18][C:19]([N:22]4[CH2:27][CH2:26][CH:25]([C:28](O)=[O:29])[CH2:24][CH2:23]4)=[N:20][CH:21]=3)[CH:14]=[CH:15][C:10]2=[N:9][C:8]=1[CH3:31].[CH3:37][S:38]([NH2:41])(=[O:40])=[O:39].Cl.C(N=C=NCCCN(C)C)C>C(Cl)Cl.CN(C)C1C=CN=CC=1>[F:1][CH:2]([F:36])[O:3][C:4]1[CH:35]=[CH:34][CH:33]=[CH:32][C:5]=1[CH2:6][C:7]1[N:11]2[CH:12]=[C:13]([C:16]3[CH:21]=[N:20][C:19]([N:22]4[CH2:27][CH2:26][CH:25]([C:28]([NH:41][S:38]([CH3:37])(=[O:40])=[O:39])=[O:29])[CH2:24][CH2:23]4)=[N:18][CH:17]=3)[CH:14]=[CH:15][C:10]2=[N:9][C:8]=1[CH3:31]

Participants

6

Reactant 3

HCID 72879MethanesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 72721708HCID 72721708, compound

Product 1

HCID 118235463HCID 118235463, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of Example 23 (0.138 g, 0.28 mmol) in DCM (6 mL) was treated with methanesulphonamide (0.1 g, 1.0 mmol 1), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (0.2 g, 1.0 mmol) and 4-(dimethylamino)pyridine (0.033 g, 0.28 mmol) and the mixture was heated to reflux for 3 days. The reaction mixture was concentrated in vacuo and the crude residue was partitioned between DCM (20 mL) and water (10 mL). The organic layer was concentrated in vacuo, and the crude residue purified by FCC on silica gel (eluting with 0-10% MeOH/DCM), to give the title compound (38 mg, 24%) as a white solid. HPLC-MS (pH 10): MH+ m/z 571.7 [M+H]+, RT 1.49 minutes.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 3 days
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customthe crude residue was partitioned between DCM (20 mL) and water (10 mL)
  5. concentrationThe organic layer was concentrated in vacuo
  6. customthe crude residue purified by FCC on silica gel (eluting with 0-10% MeOH/DCM)

Sources & evidence

ORD record
ord-5388334030c4407f8cffdc5c51d7e8d4
Source dataset
uspto-grants-2016_04
Patent number
US09309243B2

Reaction notes

Loading…