Hydrochloric Acid → HCID 49833165, compound

HRID 1947524Notes

Reaction equation

HRID 1947524 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([O:23][C:24]4[S:25][C:26]5[CH:32]=[CH:31][CH:30]=[CH:29][C:27]=5[N:28]=4)[CH:21]=3)[NH:16][CH:15]=2)[CH2:8][CH2:7]1)=[O:5])C.[OH-].[K+].Cl.C(Cl)Cl>C(O)(C)C.O>[S:25]1[C:26]2[CH:32]=[CH:31][CH:30]=[CH:29][C:27]=2[N:28]=[C:24]1[O:23][C:20]1[CH:21]=[C:22]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[C:14]2[CH2:13][CH2:12][N:9]1[CH2:10][CH2:11][CH:6]([C:4]([OH:5])=[O:3])[CH2:7][CH2:8]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 14797Potassium HydroxideHCID 49834095HCID 49834095, compound

Product 1

HCID 49833165HCID 49833165, compoundYield 104.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3776IsopropanolSolvent

Procedure

To a solution of 1-{2-[5-(benzothiazol-2-yloxy)-1H-indol-3-yl]-ethyl}-piperidine-4-carboxylic acid ethyl ester (44 mg, 0.098 mmol) in isopropanol (2.5 mL) was added H2O (1.1 mL) followed by KOH (11 mg, 0.19 mmol) in H2O (2.5 mL) and the resulting reaction mixture was stirred (rt, 16 h). The reaction mixture was acidified with 6 N HCl to pH 6 and treated with DCM (10 mL). The layers were separated and the aqueous layer was extracted with 25% isopropanol/DCM (2×10 mL). The combined organic layers were dried, filtered and concentrated in vacuo to afford the title compound as a white solid (43 mg, 100%). MS (ESI): mass calcd. for, C23H23N3O3S, 421.5; m/z found, 422.1 [M+H]+. 1H NMR (500 MHz, CD3OD): 7.76 (d, J=8.0, 1H), 7.66 (m, 2H), 7.51 (d, J=8.7, 1H), 7.43 (m, 1H), 7.36 (s, 1H), 7.31 (m, 1H), 7.16 (dd, J=8.7, 2.3, 1H), 5.20 (s, 2H), 3.94 (m, 1H), 3.30-3.14 (m, 2H), 2.54-2.30 (m, 1H), 2.23-2.04 (m, 2H), 1.30 (s, 2H), 1.17 (d, J=6.2, 4H).

Workup

  1. customthe resulting reaction mixture
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with 25% isopropanol/DCM (2×10 mL)
  4. customThe combined organic layers were dried
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fc22111f80bf404cb2b6af30e673fd6d
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

Loading…