Triethylamine → HCID 66958142, compound

HRID 1364065Notes

Reaction equation

HRID 1364065 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](Cl)=[C:14]([N+:19]([O-:21])=[O:20])[CH:15]=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[NH2:30][CH2:31][CH2:32][CH2:33][NH:34][C:35](=[O:41])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38]>>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([NH:30][CH2:31][CH2:32][CH2:33][NH:34][C:35](=[O:41])[O:36][C:37]([CH3:39])([CH3:38])[CH3:40])=[C:14]([N+:19]([O-:21])=[O:20])[CH:15]=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 2735700tert-Butyl (3-aminopropyl)carbamateHCID 210757517-(Benzyloxy)-4-chloro-3-nitroquinoline

Product 1

HCID 66958142HCID 66958142, compoundYield 95.8%

Procedure

A modification of the method described in Part E of Example 367 was used to treat 7-benzyloxy-4-chloro-3-nitroquinoline (87.81 g, 279 mmol, Parts A through D of Example 367) with triethylamine (58.3 mL, 419 mmol) and tert-butyl N-(3-aminopropyl)carbamate (58.0 g, 334 mmol). The reaction was stirred overnight at ambient temperature. After filtration, the solid was washed with water and 1:1 cold 2-propanol:water. After the drying step 120.98 g of tert-butyl 3-[(7-benzyloxy-3-nitroquinolin-4-yl)amino]propylcarbamate were obtained.

Workup

  1. filtrationAfter filtration
  2. washthe solid was washed with water and 1:1 cold 2-propanol

Sources & evidence

ORD record
ord-7bb9e7d4444447cba6ec884d00867379
Source dataset
uspto-grants-2011_02
Patent number
US07888349B2

Reaction notes

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