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Phenethylamine → HCID 57810163, compound

HRID 1924139
Notes
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Reaction equation

HRID 1924139 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH2:30])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:21][CH2:22][CH:23]3[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]3)=[C:16]([O:19][CH3:20])[CH:17]=2)[N:12]=[CH:11][CH:10]=1.CCN(CC)CC.[C:38]([O:43]CC)(=O)[C:39]([NH2:41])=[O:40].[CH2:46](N)[CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([NH:30][C:38](=[O:43])[C:39]([NH:41][CH2:46][CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)=[O:40])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:21][CH2:22][CH:23]3[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]3)=[C:16]([O:19][CH3:20])[CH:17]=2)[N:12]=[CH:11][CH:10]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 1001PhenethylamineHCID 8471TriethylamineHCID 69238Ethyl oxamateHCID 59647511HCID 59647511, compound

Product 1

HCID 57810163HCID 57810163, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
2×

Procedure

To a 0° C. solution of 3-fluoro-4-[6-methoxy-7-(1-methyl-piperidin-4-ylmethoxy)-quinolin-4-yloxy]-phenylamine (66 mg, 0.13 mmol) and Et3N (0.34 mL) in CH2Cl2 (6 mL) was added slowly ethyl oxalyl chloride (98 mg). The reaction mixture was stirred at rt for 30 min, then diluted with CH2Cl2 and washed with sat. aqueous NaHCO3. After dried over MgSO4 and concentrated, the crude ethyl oxamate was reacted with phenethylamine (80 mg, 0.64 mmol) at 80° C. for 2 h. Purification by HPLC gave product, N-{3-fluoro-4-[6-methoxy-7-(1-methyl-piperidin-4-ylmethoxy)-quinolin-4-yloxy]-phenyl}-N′-phenethyl-oxalamide (52 mg, 68% yield). 1H NMR (400 MHz) δ 9.38 (br s, 1 H), 8.48 (d, J=5.2 Hz, 1 H), 7.83 (dd, J=11.7, 2.6 Hz, 1 H), 7.59 (t, J=6.2 Hz, 1 H), 7.55 (s, 1 H), 7.40-7.20 (8 H), 6.39 (d, J=5.3 Hz, 1 H), 4.06 (d, J=6.6 Hz, 2 H), 4.04 (s, 3 H), 3.67 (q, J=6.8 Hz, 2 H), 2.98 (br d, J=11.5 Hz, 2 H), 2.92 (t, J=7.0 Hz, 2 H), 2.34 (s, 3 H), 2.10-1.80 (m, 5 H), 1.60-1.54 (m, 2 H).

Workup

  1. washwashed with sat. aqueous NaHCO3
  2. dry with materialAfter dried over MgSO4
  3. concentrationconcentrated
  4. customPurification by HPLC

Sources & evidence

ORD record
ord-36a0f95e3be5441bb03c8ef005c1b647
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08178532B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes