Hydrochloric Acid → HCID 67194659, compound

HRID 1891473Notes

Reaction equation

HRID 1891473 reaction equation
C(OC([N:8]([C@H:13]1[C:21]2[C:16](=[C:17]([C:22]3[S:23][C:24]([C:27]4[CH:32]=[CH:31][C:30]([O:33][CH:34]([CH3:36])[CH3:35])=[C:29]([C:37]#[N:38])[CH:28]=4)=[N:25][N:26]=3)[CH:18]=[CH:19][CH:20]=2)[CH2:15][CH2:14]1)[CH2:9][C:10]([OH:12])=[O:11])=O)(C)(C)C.Cl>O1CCOCC1>[C:37]([C:29]1[CH:28]=[C:27]([C:24]2[S:23][C:22]([C:17]3[CH:18]=[CH:19][CH:20]=[C:21]4[C:16]=3[CH2:15][CH2:14][C@H:13]4[NH:8][CH2:9][C:10]([OH:12])=[O:11])=[N:26][N:25]=2)[CH:32]=[CH:31][C:30]=1[O:33][CH:34]([CH3:36])[CH3:35])#[N:38]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67194218HCID 67194218, compound

Product 1

HCID 67194659HCID 67194659, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
50 °C

Procedure

To a stirred solution of (R)-2-((tert-butoxycarbonyl)(4-(5-(3-cyano-4-isopropoxyphenyl)-1,3,4-thiadiazol-2-yl)-2,3-dihydro-1H-inden-1-yl)amino)acetic acid (20 mg, 0.03) mmol in 1,4-dioxane (0.5 mL) was added 4N HCl in 1,4-dioxane (0.2 mL). The mixture was stirred at 50° C. for 2 h before it was concentrated and triturated with ether to afford 13 mg of (R)-2-((4-(5-(3-cyano-4-isopropoxyphenyl)-1,3,4-thiadiazol-2-yl)-2,3-dihydro-1H-inden-1-yl)amino)acetic acid as yellow-green solid. LCMS-ESI (m/z) calculated for C23H22N4O3S: 434.14, found 435.2 [M+H]+, tR=2.51 min.

Workup

  1. concentrationwas concentrated
  2. customtriturated with ether

Sources & evidence

ORD record
ord-88f52541c51a44e686f81a85406d26ed
Source dataset
uspto-grants-2013_08
Patent number
US08507538B2

Reaction notes

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