Hydrochloric Acid → HCID 66617396, compound

HRID 237358Notes

Reaction equation

HRID 237358 reaction equation
[ClH:1].O1CCOCC1.[CH3:8][O:9][C:10]1[CH:11]=[C:12]([NH:18][C:19]2[C:20]([NH:29][S:30]([C:33]3[CH:34]=[C:35]([NH:39][C:40](=[O:51])[C@@H:41]([NH:43]C(=O)OC(C)(C)C)[CH3:42])[CH:36]=[CH:37][CH:38]=3)(=[O:32])=[O:31])=[N:21][C:22]3[C:27]([N:28]=2)=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:13]=[C:14]([O:16][CH3:17])[CH:15]=1>C(Cl)Cl>[ClH:1].[NH2:43][C@@H:41]([CH3:42])[C:40]([NH:39][C:35]1[CH:36]=[CH:37][CH:38]=[C:33]([S:30](=[O:31])(=[O:32])[NH:29][C:20]2[C:19]([NH:18][C:12]3[CH:11]=[C:10]([O:9][CH3:8])[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=3)=[N:28][C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]=2)[CH:34]=1)=[O:51]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 59249033HCID 59249033, compound

Product 1

HCID 66617396HCID 66617396, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4 M HCl is dioxane (10 mL) was added to a solution of (S)-tert-butyl 1-(3-(N-(3-(3,5-dimethoxyphenylamino)quinoxalin-2-yl)sulfamoyl)phenylamino)-1-oxopropan-2-ylcarbamate (160 mg) and DCM (15 mL). The mixture was stirred at r.t. for 3 hours. The solvent decanted and ether added to the solid, ether decanted to gave 80 mg product as HCl salt. 1H NMR (400 MHz, CD3OD) δ 8.50-8.49 (t, 1H), 7.89-7.87 (m, 1H), 7.74-7.72 (m, 1H), 7.61-7.5 (m, 3H), 7.40-7.36 (m, 2H), 7.21-7.20 (d, 2H), 6.23-6.21 (t, 1H), 4.09-4.03 (q, 1H), 3.78 (s, 6H), 1.60-1.58 (d, 3H); MS (EI) for C25H26N6O5S.HCl: 523.1 (MH+).

Workup

  1. customThe solvent decanted
  2. additionether added to the solid, ether
  3. customdecanted

Sources & evidence

ORD record
ord-7fc025cacbff46f8ac51585d5a96943f
Source dataset
uspto-grants-2014_02
Patent number
US08642584B2

Reaction notes

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