Diisopropylethylamine → HCID 24947293, compound

HRID 1643318Notes

Reaction equation

HRID 1643318 reaction equation
[NH:1]([C:8](=[O:30])[CH2:9][N:10]([CH2:20][C:21](=[O:29])[NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:11]1[CH:19]=[CH:18][C:14]([C:15](O)=[O:16])=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C.[NH2:67][C:68]1[CH:69]=[C:70]([C:82]2[CH:87]=[CH:86][CH:85]=[CH:84][CH:83]=2)[CH:71]=[CH:72][C:73]=1[NH:74]C(=O)OC(C)(C)C>CCOC(C)=O.C(Cl)Cl.CN(C=O)C>[NH2:74][C:73]1[CH:72]=[CH:71][C:70]([C:82]2[CH:83]=[CH:84][CH:85]=[CH:86][CH:87]=2)=[CH:69][C:68]=1[NH:67][C:15](=[O:16])[C:14]1[CH:18]=[CH:19][C:11]([N:10]([CH2:20][C:21]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:29])[CH2:9][C:8](=[O:30])[NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 57717454N-(3-Amino[1,1'-biphenyl]-4-yl)-carbamic Acid tert-Butyl EsterHCID 57857116HCID 57857116, compound

Product 1

HCID 24947293HCID 24947293, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

To a solution of 4-[bis(2-anilino-2-oxoethyl)amino]benzoic acid (40 mg, 0.099 mmol) in 2:1 CH2Cl2/DMF was added BOP (66 mg, 0.149 mmol), Hunigs base (26 μL, 0.149 mmol) and tert-butyl (3-aminobipheyl-4-yl)carbamate (56 mg, 0.199 mmol) and the reaction was allowed to stir at room temperature for 12 hours. The crude reaction mixture was diluted with EtOAc (20 mL) and then washed with sat.'d aq. NaHCO3 (1×10 mL). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The crude residue was purified by reverse-phase chromatography (30-100% MeCN/H2O with 0.05% TFA). The appropriate fractions were combined, diluted with EtOAc (20 mL) and washed with sat.'d aq. NaHCO3 (1×10 mL). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo and gave the desired N-(2-aminophenyl)-4-[bis(2-anilino-2-oxoethyl)amino]benzamide: 1H NMR (600 MHz, MeOH-d4) δ 7.93 (d, J=8.9 Hz, 2H), 7.66 (dt, J=8.6, 1.5 Hz, 4H), 7.52 (d, J=7.2 Hz, 2H), 7.44 (s, 1H), 7.30 (m, 8H), 7.10 (t, J=7.8 Hz, 2H), 6.96 (d, J=7.8 Hz, 1H), 6.74 (d, J=9.1 Hz, 2H), 6.53 (t, J=7.2 Hz, 1H), 4.79 (s, 2H), 4.42 (s, 4H); MS: cal'd 570.2 (MH+), exp 570.2 (MH+).

Workup

  1. customThe crude reaction mixture
  2. washwashed with sat.'d aq. NaHCO3 (1×10 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by reverse-phase chromatography (30-100% MeCN/H2O with 0.05% TFA)
  7. additiondiluted with EtOAc (20 mL)
  8. washwashed with sat.'d aq. NaHCO3 (1×10 mL)
  9. dry with materialThe organic layer was dried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-35e8edb272df4466b39c627ccc473d00
Source dataset
uspto-grants-2012_02
Patent number
US08119685B2

Reaction notes

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