1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 178492639, compound

HRID 1096882Notes

Reaction equation

HRID 1096882 reaction equation
Cl.[NH:2]1[C:6]([C:7]2[CH:8]=[C:9]3[C:19](=[CH:20][CH:21]=2)[O:18][C:12]2([CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[CH2:11][C:10]3=[O:22])=[N:5][N:4]=[N:3]1.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[CH3:46][O:47][C:48]1[CH:49]=[C:50]([CH:54]=[C:55]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[N:56]=1)[C:51](O)=[O:52]>O.CN(C=O)C.C(N(CC)CC)C>[CH3:46][O:47][C:48]1[CH:49]=[C:50]([C:51]([N:15]2[CH2:16][CH2:17][C:12]3([CH2:11][C:10](=[O:22])[C:9]4[C:19](=[CH:20][CH:21]=[C:7]([C:6]5[NH:2][N:3]=[N:4][N:5]=5)[CH:8]=4)[O:18]3)[CH2:13][CH2:14]2)=[O:52])[CH:54]=[C:55]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[N:56]=1

Participants

8

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 579309932-Methoxy-6-phenylisonicotinic acidHCID 178479612HCID 178479612, compound

Product 1

HCID 178492639HCID 178492639, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

6-(Tetrazol-5-yl)spiro[chroman-2,4′-piperidin]-4-one hydrochloride (42 mg), 1-hydroxybenzotriazole monohydrate (20 mg), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (25 mg), triethylamine (21 μL) and water (1 mL) were added in that order to a DMF (3 mL) solution of 2-methoxy-6-phenyl-isonicotinic acid (25 mg), and stirred at room temperature for 2 hours. Water was added to the reaction liquid, the formed precipitate was taken out through filtration, washed with water, and dried to obtain the title compound as a white solid. 1H-NMR (400 MHz, DMSO-d6) δ: 8.41 (1.0H, d, J=2.0 Hz), 8.23 (1.0H, dd, J=8.6, 2.4 Hz), 8.13 (2.0H, d, J=6.8 Hz), 7.57 (1.0H, br s), 7.51-7.44 (3.0H, m), 7.32 (1.0H, d, J=8.6 Hz), 6.78 (1.0H, br s), 4.31-4.27 (1.0H, m), 3.97 (3.0H, s), 3.40-3.20 (3.0H, m), 2.97 (2.0H, s), 2.10-2.05 (1.0H, m), 1.90-1.83 (3.0H, m). MS [M−H]−=495.

Workup

  1. filtrationthe formed precipitate was taken out through filtration
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-aeece715fa3545e2b1ec0821f6324146
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

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