Diisopropylethylamine → 5-{[(3S)-1-(4-morpholinylcarbonyl)-3-pyrrolidinyl]methyl}-4-[4-(7-quinolinyl)phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 525259Notes

Reaction equation

HRID 525259 reaction equation
Cl.[NH:2]1[CH2:6][CH2:5][C@@H:4]([CH2:7][C:8]2[N:9]([C:14]3[CH:19]=[CH:18][C:17]([C:20]4[CH:29]=[C:28]5[C:23]([CH:24]=[CH:25][CH:26]=[N:27]5)=[CH:22][CH:21]=4)=[CH:16][CH:15]=3)[C:10](=[O:13])[NH:11][N:12]=2)[CH2:3]1.C(N(CC)C(C)C)(C)C.[N:39]1([C:45](Cl)=[O:46])[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1>ClCCl>[N:39]1([C:45]([N:2]2[CH2:6][CH2:5][C@@H:4]([CH2:7][C:8]3[N:9]([C:14]4[CH:15]=[CH:16][C:17]([C:20]5[CH:29]=[C:28]6[C:23]([CH:24]=[CH:25][CH:26]=[N:27]6)=[CH:22][CH:21]=5)=[CH:18][CH:19]=4)[C:10](=[O:13])[NH:11][N:12]=3)[CH2:3]2)=[O:46])[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 848104-Morpholinecarbonyl chlorideHCID 673764885-[(3S)-3-pyrrolidinylmethyl]-4-[4-(7-quinolinyl)phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one Hydrochloride

Product 1

HCID 673562425-{[(3S)-1-(4-morpholinylcarbonyl)-3-pyrrolidinyl]methyl}-4-[4-(7-quinolinyl)phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a 4 mL vial was placed 5-[(3S)-3-pyrrolidinylmethyl]-4-[4-(7-quinolinyl)phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one hydrochloride (0.147 mmol). Added in succession was dichloromethane (2 mL), N,N-diisopropylethylamine (0.458 mmol), and 4-morpholinecarbonyl chloride (0.157 mmol). The vial was capped and the solution was stirred at room temperature for 30 min. The solution was concentrated in vacuo. Reverse phase HPLC (10-70% acetonitrile/water+0.1% NH4OH) was utilized in purifying the title compound (23 mg, 31%). MS(ES)+ m/e 485.2 [M+H]+.

Workup

  1. additionAdded in succession
  2. customThe vial was capped
  3. concentrationThe solution was concentrated in vacuo
  4. customin purifying the title compound (23 mg, 31%)

Sources & evidence

ORD record
ord-b5e4864c9e94404eb9015e89af7ea085
Source dataset
uspto-grants-2016_05
Patent number
US09340529B2

Reaction notes

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