Hydrochloric Acid → HCID 86614346, compound

HRID 2236111Notes

Reaction equation

HRID 2236111 reaction equation
Cl.[CH2:2]1[C:14]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:7]([CH2:15][C:16]([O:18]CC)=[O:17])[C:6]=2[CH2:5][CH2:4][NH:3]1.[CH3:21][CH2:22]N(C(C)C)C(C)C.[C:30]1([N:36]=[C:37]=[O:38])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.Cl>ClCCl>[CH2:21]([CH:15]([N:7]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=2[C:14]2[CH2:2][N:3]([C:37](=[O:38])[NH:36][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:4][CH2:5][C:6]1=2)[C:16]([OH:18])=[O:17])[CH3:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7672Phenyl isocyanateHCID 81531DiisopropylethylamineHCID 71552668Ethyl (1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-acetate hydrochloride

Product 1

HCID 86614346HCID 86614346, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Step a): To a stirred solution of Intermediate 1 (20 mg, 0.068 mnol) and DIEA (35 μl, 0.20 mmol) in dichloromethane (1 ml) is added phenyl isocyanate (8.2 μl, 0.075 mmol). The reaction mixture is kept stirring at rt for 1 h, then 1N HCl (2 ml) was added. The aqueous layer is extracted twice with dichloromethane. The organic layers are combined and the solvent is evaporated to give crude ethyl (2-phenylcarbamoyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-acetic acid: tR (LC-2) 2.23 min; ESI-MS (positive ion): m/z 400.39 [M+Na]+ (calcd 377.44 for C22H23N3O3); 1H-NMR (CDCl3): 1.19 (t, J=7.0 Hz, 3H); 2.77 (t, J=5.3 Hz, 2H); 3.91 (t, J=5.3 Hz, 2H); 4.14 (q, J=7.0 Hz, 2H); 4.65 (s, 2H); 4.68 (s, 2H); 6.46 (s, 1H); 6.98 (t, J=7.0 Hz, 1H); 7.04-7.09 (m, 1H); 7.14-7.16 (m, 2H); 7.20-7.26 (m, 2H); 7.32-7.35 (m, 2H); 7.40 (d, J=7.6 Hz, 1H).

Workup

  1. extractionThe aqueous layer is extracted twice with dichloromethane
  2. customthe solvent is evaporated

Sources & evidence

ORD record
ord-1526a124ecdd4467a7df569bf1e5f46c
Source dataset
uspto-grants-2010_05
Patent number
US07714132B2

Reaction notes

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