Trifluoroacetic acid → HCID 86624625, compound

HRID 2354139Notes

Reaction equation

HRID 2354139 reaction equation
C(O[C:6](=O)[NH:7][CH2:8][CH2:9][C:10](=[O:19])[NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=1)(C)(C)C.[F:21][C:22]([F:27])([F:26])[C:23]([OH:25])=[O:24].[O:28]=[C:29]1[NH:38][CH:37]=[CH:36][C:35]2[N:34]=[C:33]([C:39]3[CH:46]=[CH:45][C:42](C=O)=[CH:41][CH:40]=3)[C:32]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)=[CH:31][C:30]1=2.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[F:21][C:22]([F:27])([F:26])[C:23]([O-:25])=[O:24].[OH:18][C:14]1[CH:13]=[C:12]([NH:11][C:10](=[O:19])[CH2:9][CH2:8][NH2+:7][CH2:6][C:42]2[CH:41]=[CH:40][C:39]([C:33]3[C:32]([C:47]4[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=4)=[CH:31][C:30]4[C:29](=[O:28])[NH:38][CH:37]=[CH:36][C:35]=4[N:34]=3)=[CH:46][CH:45]=2)[CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 5049666Sodium triacetoxyborohydrideHCID 592646194-(5-Oxo-3-phenyl-5,6-dihydro-1,6-naphthyridin-2-yl)benzaldehydeHCID 59380862HCID 59380862, compound

Product 1

HCID 86624625HCID 86624625, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of [2-(3-hydroxy-phenylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester (4-3) (100 mg, 0.36 mmol) in dichloromethane (2 mL) was added trifluoroacetic acid (1 mL). The suspension immediately turned into clear solution and was stirred at room temperature for 1 hr. The volatile solvents were removed by rotovap evaporation and the oil residue was further dried by vacuum pump over night. The oil residue was re-solubilized in dichloromethane (1 mL) and de-salted with triethylamine (1 mL). After the resulting solution was stirred at room temperature for 1 hr, 4-(5-oxo-3-phenyl-5,6-dihydro-1,6-naphthyridin-2-yl)benzaldehyde (4-5; synthesis shown and described in Reaction Scheme V) (80 mg, 0.25 mmol) was added followed by sodium triacetoxyborohydride (159 mg, 0.75 mmol) after an additional 0.5 hr of stirring at room temperature. The final reaction mixture was stirred at room temperature overnight and then directly purified by HPLC (Phenomenx Synergi column; 20-85% acetonitrile/water+0.1% TFA) to afford the product (4-6) as bright yellow oil: 1H-NMR (500 MHz, d4-CD3OD) δ 8.64 (s, 1H), 7.53-7.48 (m, 5H), 7.30-7.28 (m, 3H), 7.24-7.23 (m, 2H), 7.17 (m, 1H), 7.12 (m, 1H), 6.96 (m, 1H), 6.87 (m, 1H), 6.55 (m, 1H), 4.28 (s, 2H), 3.34 (m, 2H), 2.83 (m, 2H); LRMS, calc'd for C30H26N4O3 (M+1), 491.57; found 491.59.

Workup

  1. customThe volatile solvents were removed by rotovap evaporation
  2. customthe oil residue was further dried by vacuum pump over night
  3. stirringAfter the resulting solution was stirred at room temperature for 1 hr
  4. stirringof stirring at room temperature
  5. customThe final reaction mixture
  6. stirringwas stirred at room temperature overnight
  7. customdirectly purified by HPLC (Phenomenx Synergi column; 20-85% acetonitrile/water+0.1% TFA)

Sources & evidence

ORD record
ord-b2ffc822ac1446359d0e564709d61f0e
Source dataset
uspto-grants-2010_07
Patent number
US07750151B2

Reaction notes

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