Triethylamine → HCID 178466806, compound

HRID 1096889Notes

Reaction equation

HRID 1096889 reaction equation
C(N(CC)CC)C.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[CH2:31]([O:33][C:34]1[CH:35]=[C:36]([CH:40]=[CH:41][C:42]=1[C:43]1[CH:44]=[N:45][N:46]([CH3:48])[CH:47]=1)[C:37]([OH:39])=O)[CH3:32].Cl.[NH:50]1[C:54]([C:55]2[CH:56]=[C:57]3[C:67](=[CH:68][CH:69]=2)[O:66][C:60]2([CH2:65][CH2:64][NH:63][CH2:62][CH2:61]2)[CH2:59][C:58]3=[O:70])=[N:53][N:52]=[N:51]1>O.CN(C)C=O>[CH2:31]([O:33][C:34]1[CH:35]=[C:36]([C:37]([N:63]2[CH2:64][CH2:65][C:60]3([CH2:59][C:58](=[O:70])[C:57]4[C:67](=[CH:68][CH:69]=[C:55]([C:54]5[NH:53][N:52]=[N:51][N:50]=5)[CH:56]=4)[O:66]3)[CH2:61][CH2:62]2)=[O:39])[CH:40]=[CH:41][C:42]=1[C:43]1[CH:44]=[N:45][N:46]([CH3:48])[CH:47]=1)[CH3:32]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 579309863-Ethoxy-4-(1-methylpyrazol-4-yl)benzoic acidHCID 178479612HCID 178479612, compound

Product 1

HCID 178466806HCID 178466806, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Triethylamine (136 μL, 0.97 mol), 1-hydroxybenzotriazole hydrate (99.0 mg, 0.73 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (140 mg, 0.73 mol) were added to an N,N-dimethylformamide solution (4.0 mL) of 3-ethoxy-4-(1-methyl-1H-pyrazol-4-yl)benzoic acid (120 mg, 0.49 mmol) and 6-(tetrazol-5-yl)spiro[chroman-2,4′-piperidin]-4-one hydrochloride (204 mg, 0.63 mol), and then stirred at 90° C. for 30 minutes. The reaction liquid was cooled to room temperature, and water was added thereto. The formed solid was taken out through filtration, and dried overnight at 75° C. under reduced pressure to obtain the title compound as a white solid. 1H-NMR (400 MHz, DMSO-d6) δ: 8.41 (1H, d, J=2.2 Hz), 8.23 (1H, dd, J=8.5, 2.2 Hz), 8.12 (1H, s), 7.93 (1H, br s), 7.63 (1H, d, J=8.0 Hz), 7.32 (1H, d, J=8.8 Hz), 7.03 (1H, br s), 6.97 (1H, dd, J=7.9, 1.6 Hz), 4.14 (2H, q, J=6.9 Hz), 3.87 (3H, s), 3.31-3.28 (4H, m), 2.97 (2H, s), 1.92-1.79 (4H, m), 1.43 (3H, t, J=7.0 Hz). MS [M+H]+=514.

Workup

  1. customThe reaction liquid
  2. temperaturewas cooled to room temperature
  3. filtrationThe formed solid was taken out through filtration
  4. customdried overnight at 75° C. under reduced pressure

Sources & evidence

ORD record
ord-c1d0c577c88347a6b4aef82dc9be4263
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

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