Triethylamine → HCID 118329947, compound

HRID 1778313Notes

Reaction equation

HRID 1778313 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)[C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[NH:15][C:14](=[O:19])[CH:13]=[C:12]3[NH:20][CH:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)=[CH:4][CH:3]=1.[C:34]([O:38][C:39]([NH:41][C:42]([NH:44][C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])=S)=[O:40])([CH3:37])([CH3:36])[CH3:35].C(N(CC)CC)C>CN(C=O)C>[Cl:33][C:30]1[CH:29]=[CH:28][C:27]([CH:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[NH:15][C:14](=[O:19])[CH:13]=[C:12]3[NH:20][CH:21]2[CH2:22][CH2:23][N:24](/[C:42](/[NH:44][C:45](=[O:46])[O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[N:41]\[C:39]([O:38][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:40])[CH2:25][CH2:26]2)=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5193990N,N'-Di-Boc-thioureaHCID 118323976HCID 118323976, compound

Product 1

HCID 118329947HCID 118329947, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 6-(bis(4-chlorophenyl)methyl)-4-(piperidin-4-ylamino)quinolin-2(1H)-one (250 mg, 0.523 mmol0, N,N′-bis-tert-butoxycarbonylthiourea (158.8 mg, 0.575 mmol) and triethylamine (0.22 mL, 1.57 mmol) in 3 mL DMF was added mercuric chloride (170.2 mg, 0.63 mmol) at 0° C. The reaction was stirred for 3 h at 0° C. and then quenched with EtOAc. The reaction was filtered through CELITE. The filtrate was washed two times with water, then dried over anhydrous Na2SO4, filtered and concentrated. The resulting residue was purified on ISCO with MeOH—CH2Cl2 and re-purified on HPLC (40-90% CH3CN (0.1% TFA)/H2O (0.1% TFA)) to yield (Z)-tert-butyl ((4-((6-(bis(4-chlorophenyl)methyl)-2-oxo-1,2-dihydroquinolin-4-yl)amino)piperidin-1-yl)((tert-butoxycarbonyl)imino)methyl)carbamate.

Workup

  1. customquenched with EtOAc
  2. filtrationThe reaction was filtered through CELITE
  3. washThe filtrate was washed two times with water
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was purified on ISCO with MeOH—CH2Cl2
  8. customre-purified on HPLC (40-90% CH3CN (0.1% TFA)/H2O (0.1% TFA))

Sources & evidence

ORD record
ord-f01628f2a5cb4bb192f628ce8d877cf1
Source dataset
uspto-grants-2016_02
Patent number
US09266835B2

Reaction notes

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