Triethylamine → HCID 178515381, compound

HRID 1096881Notes

Reaction equation

HRID 1096881 reaction equation
C(N(CC)CC)C.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[F:31][C:32]1[CH:37]=[CH:36][C:35]([C:38]2[CH:43]=[C:42]([C:44]([OH:46])=O)[CH:41]=[C:40]([C:47]3[CH:52]=[CH:51][C:50]([F:53])=[CH:49][CH:48]=3)[N:39]=2)=[CH:34][CH:33]=1.Cl.[NH:55]1[C:59]([C:60]2[CH:61]=[C:62]3[C:72](=[CH:73][CH:74]=2)[O:71][C:65]2([CH2:70][CH2:69][NH:68][CH2:67][CH2:66]2)[CH2:64][C:63]3=[O:75])=[N:58][N:57]=[N:56]1>CN(C)C=O>[F:53][C:50]1[CH:49]=[CH:48][C:47]([C:40]2[CH:41]=[C:42]([C:44]([N:68]3[CH2:69][CH2:70][C:65]4([CH2:64][C:63](=[O:75])[C:62]5[C:72](=[CH:73][CH:74]=[C:60]([C:59]6[NH:58][N:57]=[N:56][N:55]=6)[CH:61]=5)[O:71]4)[CH2:66][CH2:67]3)=[O:46])[CH:43]=[C:38]([C:35]3[CH:34]=[CH:33][C:32]([F:31])=[CH:37][CH:36]=3)[N:39]=2)=[CH:52][CH:51]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 463137012,6-Bis(4-fluorophenyl)pyridine-4-carboxylic acidHCID 178479612HCID 178479612, compound

Product 1

HCID 178515381HCID 178515381, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Triethylamine (71.0 μl, 0.51 mol), 1-hydroxybenzotriazole hydrate (35 mg, 0.26 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (49.0 mg, 0.26 mol) were added to an N,N-dimethylformamide solution (0.5 mL) of 2,6-bis(4-fluorophenyl)pyridine-4-carboxylic acid (53.0 mg, 0.17 mmol) and 6-(tetrazol-5-yl)spiro[chroman-2,4′-piperidin]-4-one hydrochloride (82.0 mg, 0.26 mol), and stirred at 60° C. for 3 hours. The reaction liquid was concentrated under reduced pressure, and the resulting residue was purified through high-performance preparative liquid chromatography (0.1% TFA, water/acetonitrile) to obtain the title compound as a white solid. 1H-NMR (400 MHz, DMSO-d6) δ: 8.42 (1H, d, J=2.0 Hz), 8.31 (4H, dd, J=8.7, 5.7 Hz), 8.25 (1H, dd, J=8.7, 2.3 Hz), 7.94 (2H, s), 7.39-7.33 (5H, m), 4.35-4.32 (1H, m), 3.46-3.32 (3H, m), 2.99 (2H, s), 2.13-2.10 (1H, m), 1.91-1.87 (3H, m). MS [M+H]+=579.

Workup

  1. customThe reaction liquid
  2. concentrationwas concentrated under reduced pressure
  3. customthe resulting residue was purified through high-performance preparative liquid chromatography (0.1% TFA, water/acetonitrile)

Sources & evidence

ORD record
ord-91ffbacd49964572979697676b988a5e
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

Loading…