Triethylamine → HCID 18791478, compound

HRID 1005594Notes

Reaction equation

HRID 1005594 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:49]=[CH:48][CH:47]=[CH:46][C:14]=1[C:15]([NH:17][C:18]1[CH:43]=[CH:42][C:21]([C:22]([N:24]([CH3:41])[C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][C:26]=2[O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][C:38]([OH:40])=O)=[O:23])=[CH:20][C:19]=1[O:44][CH3:45])=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:57][N:58]1[CH2:63][CH2:62][NH:61][CH2:60][CH2:59]1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1>C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:49]=[CH:48][CH:47]=[CH:46][C:14]=1[C:15]([NH:17][C:18]1[CH:43]=[CH:42][C:21]([C:22]([N:24]([CH3:41])[C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][C:26]=2[O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][C:38]([N:61]2[CH2:62][CH2:63][N:58]([CH3:57])[CH2:59][CH2:60]2)=[O:40])=[O:23])=[CH:20][C:19]=1[O:44][CH3:45])=[O:16])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 199401P,P-Diphenylphosphinic azideHCID 18791200HCID 18791200, compound

Product 1

HCID 18791478HCID 18791478, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-[2-[(3-tert-butoxycarbonylaminoprop-1-yl)oxy]benzoyl]amino-3-methoxy-N-methyl-N-[2-(5-carboxypent-1-yloxy)-4-methylphenyl]benzamide (3.5 g) in ethyl acetate (30 ml) was treated at ambient temperature with triethylamine (575 mg), N-methylpiperazine (569 mg), and diphenylphosphoryl azide (1.56 g). The reaction mixture was stirred at the same temperature for 17 hours. The reaction mixture was washed with brine and dried over magnesium sulfate. The crude product was purified by silica gel column chromatography (SiO2 100 g, 3% methanol in chloroform) to give 4-[2-[(3-tert-butoxycarbonylaminoprop-1-yl)oxy]benzoyl]amino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide (2.93 g).

Workup

  1. washThe reaction mixture was washed with brine
  2. dry with materialdried over magnesium sulfate
  3. customThe crude product was purified by silica gel column chromatography (SiO2 100 g, 3% methanol in chloroform)

Sources & evidence

ORD record
ord-b829e30a903e4f53a9471e630ef362d3
Source dataset
uspto-grants-2000_04
Patent number
US06054457

Reaction notes

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