4-Bromoaniline → (E)-[2-(3-{4-[1-(4-Bromo-phenylcarbamoyl)-3-(tert-butyl-dimethyl-silanyloxy)-propyl]-phenyl}-acryloylamino)-phenyl]-carbamic acid tert-butyl ester

HRID 220173Notes

Reaction equation

HRID 220173 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](/[CH:18]=[CH:19]/[C:20]1[CH:25]=[CH:24][C:23]([CH:26]([CH2:30][CH2:31][O:32][Si:33]([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34])[C:27](O)=[O:28])=[CH:22][CH:21]=1)=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[Br:61][C:62]1[CH:67]=[CH:66][C:65]([NH2:68])=[CH:64][CH:63]=1>C(Cl)Cl>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:17])/[CH:18]=[CH:19]/[C:20]1[CH:25]=[CH:24][C:23]([CH:26]([C:27](=[O:28])[NH:68][C:65]2[CH:66]=[CH:67][C:62]([Br:61])=[CH:63][CH:64]=2)[CH2:30][CH2:31][O:32][Si:33]([C:36]([CH3:38])([CH3:37])[CH3:39])([CH3:34])[CH3:35])=[CH:22][CH:21]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 78074-BromoanilineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 59238283(E)-2-{4-[2-(2-tert-Butoxycarbonylamino-phenylcarbamoyl)-vinyl]-phenyl}-4-(tert-butyl-dimethyl-silanyloxy)-butyric acid

Product 1

HCID 59238282(E)-[2-(3-{4-[1-(4-Bromo-phenylcarbamoyl)-3-(tert-butyl-dimethyl-silanyloxy)-propyl]-phenyl}-acryloylamino)-phenyl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (E)-2-{4-[2-(2-tert-butoxycarbonylamino-phenylcarbamoyl)-vinyl]-phenyl}-4-(tert-butyl-dimethyl-silanyloxy)-butyric acid (2.5 g, 4.52 mmol), EDCI (1.2 g, 4.97 mmol) and HOBt (671 mg, 4.97 mol) in CH2Cl2 (50 mL) was added 4-bromo-phenylamine (786 mg, 4.57 mmol). This mixture was stirred overnight at room temperature and then diluted with CH2Cl2 (50 mL), washed with saturated aqueous NaHCO3 solution, water and brine, dried with Na2SO4, and evaporated to obtain a yellow residue. MS: calc'd 708 (MH+), exp 708 (MH+).

Workup

  1. washwashed with saturated aqueous NaHCO3 solution, water and brine
  2. dry with materialdried with Na2SO4
  3. customevaporated
  4. customto obtain a yellow residue

Sources & evidence

ORD record
ord-b6c9893f379945cf9d871c999278b1b5
Source dataset
uspto-grants-2012_06
Patent number
US08202866B2

Reaction notes

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