Hydrochloric Acid → HCID 53233437, compound

HRID 1891469Notes

Reaction equation

HRID 1891469 reaction equation
[Si]([O:8][CH2:9][CH2:10][NH:11][C@@H:12]1[C:20]2[C:15](=[C:16]([C:21]3[S:25][C:24]([C:26]4[CH:27]=[CH:28][C:29]([O:34][CH:35]([CH3:37])[CH3:36])=[C:30]([CH:33]=4)[C:31]#[N:32])=[N:23][CH:22]=3)[CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13]1)(C(C)(C)C)(C)C.Cl>CCOCC>[OH:8][CH2:9][CH2:10][NH:11][C@@H:12]1[C:20]2[C:15](=[C:16]([C:21]3[S:25][C:24]([C:26]4[CH:27]=[CH:28][C:29]([O:34][CH:35]([CH3:37])[CH3:36])=[C:30]([CH:33]=4)[C:31]#[N:32])=[N:23][CH:22]=3)[CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58367305HCID 58367305, compound

Product 1

HCID 53233437HCID 53233437, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of (S)-5-(5-(1-((2-((tert-butyldimethylsilyl)oxy)ethyl)amino)-2,3-dihydro-1H-inden-4-yl)thiazol-2-yl)-2-isopropoxybenzonitrile (10 mg, 0.018 mmol) in ether (1 mL) was added 2N HCl in ether (0.1 mL). The mixture was stirred at room temperature for 12 h and solvent was evaporated. The crude material was purified by a preparative HPLC to afford 6 mg (80%) of (S)-5-(5-(1-((2-hydroxyethyl)amino)-2,3-dihydro-1H-inden-4-yl)thiazol-2-yl)-2-isopropoxybenzonitrile 92. LCMS-ESI (m/z) calculated for: C24H25N3O2S: 419.2; found 420.2 [M+H]+, tR=2.43 min.

Workup

  1. customsolvent was evaporated
  2. customThe crude material was purified by a preparative HPLC

Sources & evidence

ORD record
ord-9a1f6dae4d964221abee944a47ea089c
Source dataset
uspto-grants-2013_08
Patent number
US08507538B2

Reaction notes

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