Hydrochloric Acid → HCID 178478751, compound

HRID 1922504Notes

Reaction equation

HRID 1922504 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[NH:30])[NH:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH:18]1[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19]1)[CH2:13][CH2:12][CH2:11]2.[ClH:31]>CO>[ClH:31].[ClH:31].[NH:20]1[CH2:21][CH2:22][CH:18]([N:14]2[C:15]3[C:10](=[CH:9][C:8]([NH:7][C:6]([C:2]4[S:1][CH:5]=[CH:4][CH:3]=4)=[NH:30])=[CH:17][CH:16]=3)[CH2:11][CH2:12][CH2:13]2)[CH2:19]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178452051HCID 178452051, compound

Product 1

HCID 178478751HCID 178478751, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
90 °C

Procedure

A solution of tert-butyl 3-(6-(thiophene-2-carboximidamido)-3,4-dihydroquinolin-1(2H)-yl)pyrrolidine-1-carboxylate (Isomer 1) (520 mg, 1.219 mmol) in MeOH (26 ml) was treated with 3N HCl (4.06 ml, 12.19 mmol) then heated at 90° C. for 30 minutes. After cooling, the mixture was concentrated to dryness and dried under reduced pressure overnight. The solid was triturated with 5% isopropanol/95% hexanes (50 mL), collected and dried under reduced pressure (450 mg, 92%). ESI-MS (m/z, %) 327.2 (MH+, 65%), 258.1 (100%); ESI-HRMS calculated for C18H23N4S (MH+), Calculated: 327.1637; Observed: 326.1650; Chemical purity: 97.7%; Optical Rotation: 25[α]589=−0.19°, c=1.05 in MeOH.

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated to dryness
  3. customdried under reduced pressure overnight
  4. customThe solid was triturated with 5% isopropanol/95% hexanes (50 mL)
  5. customcollected
  6. customdried under reduced pressure (450 mg, 92%)
  7. custom25[α]589=−0.19°, c=1.05 in MeOH

Sources & evidence

ORD record
ord-efe66d7f956041f79657f64d3d4a9de8
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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