3-Aminoquinoline → HCID 67520350, compound

HRID 1923987Notes

Reaction equation

HRID 1923987 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1)[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:27][C:28]1[CH:29]=[N:30][C:31]2[C:36]([CH:37]=1)=[CH:35][CH:34]=[CH:33][CH:32]=2.C[N+]1(C2N=C(OC)N=C(OC)N=2)CCOCC1.[Cl-]>C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:10](=[O:12])[NH:27][C:28]1[CH:29]=[N:30][C:31]2[C:36]([CH:37]=1)=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:13][CH:14]1[CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:18][CH2:19]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 113753-AminoquinolineHCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 27281612HCID 27281612, compound

Product 1

HCID 67520350HCID 67520350, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-{1-[(tert-butoxy)carbonyl]piperidin-4-yl}propanoic acid LXXV (450 mg 1.21 mmol) and 3-aminoquinoline (187 mg, 1.30 mmol) in DCM (20 mL) was added DMT-MM (387 mg, 1.4 mmol). The mixture was stirred at r.t. overnight. The reaction was washed with water, 1 N HCl, satd. aq. NaHCO3, water and dried over Na2SO4. The product was purified on a silica gel column (1:1 EtOAc:hexane) to give tert-butyl 4-[(2S)-2-{[(tert-butoxy)carbonyl]amino}-2-[(quinolin-3-yl)carbamoyl]ethyl]piperidine-1-carboxylate (425 mg, 0.85 mmol, 70% yield). 1H NMR (DMSO-d6) 1.02-1.10 (m, 2H), 1.40 (s, 18H), 1.54-1.73 (m, 9H), 4.22-4.25 (m, 1H), 7.20 (d, J=8 Hz, 1H), 7.55-7.66 (m, 2H), 7.94 (t, J=8 Hz, 2H), 8.69 (d, J=2 Hz, 1H), 8.93 (d, J=2 Hz, 1H), 10.44 (s, 1H). ESIMS found for C27H38N4O5 m/z 499 (M+H).

Workup

  1. washThe reaction was washed with water, 1 N HCl
  2. dry with materialaq. NaHCO3, water and dried over Na2SO4
  3. customThe product was purified on a silica gel column (1:1 EtOAc:hexane)

Sources & evidence

ORD record
ord-6b69cf71ef7149e9b72ffac37a4ca646
Source dataset
uspto-grants-2012_05
Patent number
US08178490B2

Reaction notes

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