Hydrochloric Acid → HCID 89525975, compound

HRID 920267Notes

Reaction equation

HRID 920267 reaction equation
[S:1]1[C:5]([NH:6][S:7]([C:10]2[C:40]([Cl:41])=[CH:39][C:13]3[N:14]([C@@H:18]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[C:26]4[CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28][CH:27]=4)[CH3:19])[C:15](=[O:17])[O:16][C:12]=3[CH:11]=2)(=[O:9])=[O:8])=[N:4][CH:3]=[N:2]1.C(Cl)Cl.Cl.CCOC(C)=O>CO>[ClH:41].[Cl:41][C:40]1[C:10]([S:7]([NH:6][C:5]2[S:1][N:2]=[CH:3][N:4]=2)(=[O:9])=[O:8])=[CH:11][C:12]2[O:16][C:15](=[O:17])[N:14]([C@@H:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH:27]=3)[CH3:19])[C:13]=2[CH:39]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 89526135HCID 89526135, compound

Product 1

HCID 89525975HCID 89525975, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a flask containing (R)-tert-butyl 4-(2-(1-(6-(N-(1,2,4-thiadiazol-5-yl)sulfamoyl)-5-chloro-2-oxobenzo[d]oxazol-3(2H)-yl)ethyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate (34-5) (16 mg, 0.026 mmol) (prepared by a sequence analogous to the synthesis of 16-4, vide supra) was added DCM (2 ml) & MeOH (2), then added saturated HCl in EtOAc (˜4N) (64.7 μl, 0.26 mmol). The reaction mixture was capped (not under N2) & stirred at room temperature. Followed by LC/MS. After 3 hours the reaction mixture was concentrated to yield (R)-5-chloro-2-oxo-3-(1-(2-(1,2,3,6-tetrahydropyridin-4-yl)phenyl)ethyl)-N-(1,2,4-thiadiazol-5-yl)-2,3-dihydrobenzo[d]oxazole-6-sulfonamide hydrochloride (34-6). HRMS [M+H] calculated; 518.0718, observed; 518.0706. 1H NMR (499 MHz, DMSO): δ 9.15 (d, J=33.1 Hz, 2H); 8.51 (s, 1H); 7.95 (s, 1H); 7.79 (d, J=7.7 Hz, 1H); 7.63-7.46 (m, 2H); 7.46-7.36 (m, 2H); 7.23 (s, 1H); 7.09 (d, J=7.3 Hz, 1H); 5.74-5.68 (m, 1H); 5.42 (br s, 1H); 3.65-3.54 (m, 1H); 3.35-3.23 (m, 1H); 3.18-3.09 (m, 2H); 2.67-2.55 (m 1H); 2.18-2.08 (m, 1H); 1.83 (d, J=7.1 Hz, 3H). Note: NMR peaks overlapping with solvent or water could not be accurately accounted for.

Workup

  1. customprepared by a sequence analogous to the synthesis of 16-4, vide supra)
  2. customThe reaction mixture was capped (not under N2) &
  3. concentrationAfter 3 hours the reaction mixture was concentrated

Sources & evidence

ORD record
ord-4b315a149cc247a896ab7ba4dfa62703
Source dataset
uspto-grants-2016_03
Patent number
US09273040B2

Reaction notes

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