Hydrochloric Acid → HCID 178427334, compound

HRID 2174031Notes

Reaction equation

HRID 2174031 reaction equation
[C:1]([C:3]1[CH:41]=[CH:40][C:6]2[N:7]=[C:8]([C:10]([NH:33]S(C(C)(C)C)=O)([C:12]3[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[C:17]4[C:13]=3[CH:14]=[CH:15][N:16]4[S:23]([C:26]3[CH:32]=[CH:31][C:29]([CH3:30])=[CH:28][CH:27]=3)(=[O:25])=[O:24])[CH3:11])[NH:9][C:5]=2[CH:4]=1)#[N:2].Cl>>[NH2:33][C:10]([C:8]1[NH:7][C:6]2[CH:40]=[CH:41][C:3]([C:1]#[N:2])=[CH:4][C:5]=2[N:9]=1)([C:12]1[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[C:17]2[C:13]=1[CH:14]=[CH:15][N:16]2[S:23]([C:26]1[CH:27]=[CH:28][C:29]([CH3:30])=[CH:31][CH:32]=1)(=[O:25])=[O:24])[CH3:11]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 86701640HCID 86701640, compound

Product 1

HCID 178427334HCID 178427334, compound

Procedure

A solution of (±)-N-(1-(5-cyanobenzo[d]imidazol-2-yl)-1-(5,7-dimethyl-1-tosyl-1H-indol-4-yl)ethyl)-2-methylpropane-2-sulfinamide (97 mg, 0.165 mmol) and HCl (1.25 M in MeOH) (792 μL, 0.990 mmol) was allowed to stir at rt for 17 h. The mixture was concentrated and then diluted with 1 M aq. NaOH, brine and CH2Cl2. The organic layer was separated and concentrated. The residue was purified by flash column chromatography on silica gel (CH2Cl2/MeOH=100:0 to 10:1) to give the title compound. MS (ESI+) m/z 484.44 (M+H).

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with 1 M aq. NaOH, brine and CH2Cl2
  3. customThe organic layer was separated
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography on silica gel (CH2Cl2/MeOH=100:0 to 10:1)

Sources & evidence

ORD record
ord-9e65f1048fd246158a4af4d5099de9e8
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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