Hydrochloric Acid → HCID 58367143, compound

HRID 1891500Notes

Reaction equation

HRID 1891500 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:13]2[S:17][C:16]([C:18]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:19]=3[CH2:20][CH2:21][C@H:22]4[NH:27]C(=O)OC(C)(C)C)=[CH:15][CH:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11])#[N:2].Cl>O1CCOCC1>[NH2:27][C@H:22]1[C:23]2[C:19](=[C:18]([C:16]3[S:17][C:13]([C:5]4[CH:6]=[CH:7][C:8]([O:9][CH:10]([CH3:12])[CH3:11])=[C:3]([CH:4]=4)[C:1]#[N:2])=[CH:14][CH:15]=3)[CH:26]=[CH:25][CH:24]=2)[CH2:20][CH2:21]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58367241HCID 58367241, compound

Product 1

HCID 58367143HCID 58367143, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

Prepared using General Procedure 5. To a stirred solution of (R)-tert-butyl 4-(5-(3-cyano-4-isopropoxyphenyl)thiophen-2-yl)-2,3-dihydro-1H-inden-1-ylcarbamate (15 mg, 0.03 mmol) in 1,4-dioxane (1 mL) was added 4N HCl solution in 1,4-dioxane (0.5 mL). The reaction mixture was stirred at room temperature for 16 h. Solvent was evaporated the resulting solid was dissolved 1:1 DMSO:MeOH (1 mL) and purified by preparative HPLC to afford 10 mg (90%) of (R)-5-(5-(1-amino-2,3-dihydro-1H-inden-4-yl)thiophen-2-yl)-2-isopropoxybenzonitrile 225 as a white solid. LCMS-ESI (m/z) calculated for C23H22N2OS: 374.2; found 358.1. [M-NH2]+, tR=2.69 min.

Workup

  1. customPrepared
  2. customSolvent was evaporated the resulting solid
  3. dissolutionwas dissolved 1:1 DMSO
  4. customMeOH (1 mL) and purified by preparative HPLC

Sources & evidence

ORD record
ord-d2f05a90c3c34d6da9ba4914acc62306
Source dataset
uspto-grants-2013_08
Patent number
US08507538B2

Reaction notes

Loading…