1-Hydroxybenzotriazole → 1'-{[4-(2-Methyl-1,3-oxazol-5-yl)-3,5-dimethoxyphenyl]carbonyl}-6-(tetrazol-5-yl)spiro[chroman-2,4'-piperidin]-4-one

HRID 1096903Notes

Reaction equation

HRID 1096903 reaction equation
C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[CH3:23][C:24]1[O:25][C:26]([C:29]2[C:37]([O:38][CH3:39])=[CH:36][C:32]([C:33]([OH:35])=O)=[CH:31][C:30]=2[O:40][CH3:41])=[CH:27][N:28]=1.Cl.[NH:43]1[C:47]([C:48]2[CH:49]=[C:50]3[C:60](=[CH:61][CH:62]=2)[O:59][C:53]2([CH2:58][CH2:57][NH:56][CH2:55][CH2:54]2)[CH2:52][C:51]3=[O:63])=[N:46][N:45]=[N:44]1>O.CN(C=O)C.CCN(CC)CC>[CH3:23][C:24]1[O:25][C:26]([C:29]2[C:30]([O:40][CH3:41])=[CH:31][C:32]([C:33]([N:56]3[CH2:57][CH2:58][C:53]4([CH2:52][C:51](=[O:63])[C:50]5[C:60](=[CH:61][CH:62]=[C:48]([C:47]6[NH:46][N:45]=[N:44][N:43]=6)[CH:49]=5)[O:59]4)[CH2:54][CH2:55]3)=[O:35])=[CH:36][C:37]=2[O:38][CH3:39])=[CH:27][N:28]=1

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 579310004-(2-Methyl-1,3-oxazol-5-yl)-3,5-dimethoxybenzoic acidHCID 178479612HCID 178479612, compound

Product 1

HCID 1784926401'-{[4-(2-Methyl-1,3-oxazol-5-yl)-3,5-dimethoxyphenyl]carbonyl}-6-(tetrazol-5-yl)spiro[chroman-2,4'-piperidin]-4-one

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

Et3N (28 μL), HOBT (15 mg) and WSC hydrochloride (19 mg) were added to a DMF (3 mL) solution of 4-(2-methyl-1,3-oxazol-5-yl)-3,5-dimethoxybenzoic acid (22 mg) and 6-(tetrazol-5-yl)spiro[chroman-2,4′-piperidin]-4-one hydrochloride (32 mg), and stirred overnight at room temperature. Water was added to the reaction liquid, the formed solid was taken out through filtration, and the solid was washed with water and ether. The solid was dried under reduced pressure to obtain the title compound. 1H-NMR (400 MHz, DMSO-d6) δ: 8.42 (1H, d, J=4.0 Hz), 8.23 (1H, dd, J=8.0, 4.0 Hz), 7.32 (1H, d, J=8.0 Hz), 7.08 (1H, s), 6.75 (2H, s), 4.32-4.18 (1H, m), 3.79 (6H, s), 3.64-3.20 (3H, m), 2.97 (2H, s), 2.41 (3H, s), 2.10-1.75 (4H, m). MS [M+H]+=531.

Workup

  1. filtrationthe formed solid was taken out through filtration
  2. washthe solid was washed with water and ether
  3. customThe solid was dried under reduced pressure

Sources & evidence

ORD record
ord-fc3d1a0216b34257a1ceb544889ee1df
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

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