Water → HCID 66958805, compound

HRID 1364059Notes

Reaction equation

HRID 1364059 reaction equation
C(N(CC)CC)C.[CH3:8][C:9]([O:12][C:13]([NH:15][CH2:16][CH2:17][NH2:18])=[O:14])([CH3:11])[CH3:10].[CH2:19]([O:26][C:27]1[CH:36]=[C:35]2[C:30]([C:31](Cl)=[C:32]([N+:37]([O-:39])=[O:38])[CH:33]=[N:34]2)=[CH:29][CH:28]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>CN(C=O)C>[CH2:19]([O:26][C:27]1[CH:36]=[C:35]2[C:30]([C:31]([NH:18][CH2:17][CH2:16][NH:15][C:13](=[O:14])[O:12][C:9]([CH3:8])([CH3:10])[CH3:11])=[C:32]([N+:37]([O-:39])=[O:38])[CH:33]=[N:34]2)=[CH:29][CH:28]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 187201N-BOC-ethylenediamineHCID 210757517-(Benzyloxy)-4-chloro-3-nitroquinoline

Product 1

HCID 66958805HCID 66958805, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Triethylamine (58.9 mL, 422.4 mmol, 1.5 eq) and tert-butyl N-(2-aminoethyl) carbamate (54.1 g, 337.9 mmol, 1.2 eq) were added sequentially to a solution of 7-benzyloxy-4-chloro-3-nitroquinoline (88.63 g, 281.6 mmol) in DMF (800 mL) and stirred for 4 hours at ambient temperature. The crude reaction mixture was poured into hot water with continuous stirring to afford bright a yellow precipitate. The yellow solid was filtered and dried under reduced pressure at 65° C. to afford 123.65 g of tert-butyl 2-[(7-benzyloxy-3-nitroquinolin-4-yl)amino]ethylcarbamate.

Workup

  1. customThe crude reaction mixture
  2. stirringwith continuous stirring
  3. customto afford bright a yellow precipitate
  4. filtrationThe yellow solid was filtered
  5. customdried under reduced pressure at 65° C.

Sources & evidence

ORD record
ord-17a19d47ba0642829b8416ba621cb699
Source dataset
uspto-grants-2011_02
Patent number
US07888349B2

Reaction notes

Loading…