1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 6-(1-Methylethyl)-1'-{[5-(tetrazol-5-yl)biphenyl-3-yl]carbonyl}spiro[7-azachroman-2,4'-piperidin]-4-one

HRID 1096887Notes

Reaction equation

HRID 1096887 reaction equation
Cl.[CH3:2][CH:3]([C:5]1[CH:6]=[C:7]2[C:17](=[CH:18][N:19]=1)[O:16][C:10]1([CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)[CH2:9][C:8]2=[O:20])[CH3:4].O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[NH:44]1[C:48]([C:49]2[CH:50]=[C:51]([C:61](O)=[O:62])[CH:52]=[C:53]([C:55]3[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=3)[CH:54]=2)=[N:47][N:46]=[N:45]1>O.CN(C=O)C.C(N(CC)CC)C>[CH3:4][CH:3]([C:5]1[CH:6]=[C:7]2[C:17](=[CH:18][N:19]=1)[O:16][C:10]1([CH2:11][CH2:12][N:13]([C:61]([C:51]3[CH:52]=[C:53]([C:55]4[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=4)[CH:54]=[C:49]([C:48]4[NH:47][N:46]=[N:45][N:44]=4)[CH:50]=3)=[O:62])[CH2:14][CH2:15]1)[CH2:9][C:8]2=[O:20])[CH3:2]

Participants

8

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 667817546-(1-Methylethyl)spiro[7-azachroman-2,4'-piperidin]-4-one hydrochlorideHCID 178524111HCID 178524111, compound

Product 1

HCID 1784383886-(1-Methylethyl)-1'-{[5-(tetrazol-5-yl)biphenyl-3-yl]carbonyl}spiro[7-azachroman-2,4'-piperidin]-4-one

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
90 °C

Procedure

6-(1-Methylethyl)spiro[7-azachroman-2,4′-piperidin]-4-one hydrochloride (94 mg), 1-hydroxybenzotriazole monohydrate (36 mg), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (57 mg), triethylamine (73 μL) and water (1 mL) were added in that order to a DMF (3 mL) solution of 5-(tetrazol-5-yl)biphenyl-3-carboxylic acid (50 mg), and stirred at 90° C. for 1 hour and 30 minutes. Water was added to the reaction liquid, the formed precipitate was taken out through filtration, washed with hexane/ethyl acetate=2/1, and dried to obtain the title compound as a white solid. 1H-NMR (400 MHz, DMSO-d6) δ: 8.50 (1.0H, s), 8.38 (1.0H, s), 8.04 (1.0H, s), 7.87 (1.0H, s), 7.79 (2.0H, d, J=7.6 Hz), 7.54 (2H, t, J=7.6 Hz), 7.45 (1.011, t, J=7.6 Hz), 7.40 (1.0H, s), 4.40-4.22 (1.0H, m), 3.65-3.20 (3.0H, m), 3.01 (1.0H, q, J=6.8 Hz), 2.97 (2.0H, s), 2.15-2.05 (1.0H, m), 1.95-1.78 (3.0H, m), 1.18 (6.0H, d, J=6.8 Hz). MS [M+H]+=509.

Workup

  1. filtrationthe formed precipitate was taken out through filtration
  2. washwashed with hexane/ethyl acetate=2/1
  3. customdried

Sources & evidence

ORD record
ord-bc08f5ee55cc4fcda7264cee81c5d674
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

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