Triethylamine → HCID 178480022, compound

HRID 1096888Notes

Reaction equation

Cl.[CH3:2][N:3]1[CH:7]=[C:6]([C:8]2[CH:9]=[C:10]3[C:20](=[CH:21][CH:22]=2)[O:19][C:13]2([CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[CH2:12][C:11]3=[O:23])[CH:5]=[N:4]1.O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.[NH:42]1[C:46]([C:47]2[CH:48]=[C:49]([C:59](O)=[O:60])[CH:50]=[C:51]([C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)[CH:52]=2)=[N:45][N:44]=[N:43]1>O.CN(C=O)C>[CH3:2][N:3]1[CH:7]=[C:6]([C:8]2[CH:9]=[C:10]3[C:20](=[CH:21][CH:22]=2)[O:19][C:13]2([CH2:14][CH2:15][N:16]([C:59]([C:49]4[CH:50]=[C:51]([C:53]5[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=5)[CH:52]=[C:47]([C:46]5[NH:45][N:44]=[N:43][N:42]=5)[CH:48]=4)=[O:60])[CH2:17][CH2:18]2)[CH2:12][C:11]3=[O:23])[CH:5]=[N:4]1

Participants

Conditions

Temperature: 90 °C

Procedure

6-(1-Methyl-1H-pyrazol-4-yl)spiro[chroman-2,4′-piperidin]-4-one hydrochloride (93 mg), 1-hydroxybenzotriazole monohydrate (36 mg), 1-(3-dimethyl aminopropyl)-3-ethylcarbodiimide hydrochloride (57 mg), triethylamine (0.73 mL) 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 2 hours and 30 minutes. Water was added to the reaction liquid, and the formed precipitate was taken out through filtration, washed with hexane/ethyl acetate=3/2, and dried to obtain the title compound as a white solid. 1H-NMR (400 MHz, DMSO-d6) δ: 8.36 (1.0H, s), 8.13 (1.0H, s), 8.03 (1.0H, s), 7.85-7.77 (6.0H, m), 7.53 (2.0H, d, J=7.2 Hz), 7.44 (1.0H, t, J=7.2 Hz), 7.10 (1.0H, d, J=8.4 Hz), 4.40-4.22 (1.0H, m), 3.83 (3.0H, s), 3.65-3.20 (3.0H, m), 2.89 (2.0H, s), 2.15-2.05 (1.0H, m), 1.95-1.78 (3.0H, m). MS [M+H]+=546.

Workup

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

Sources & evidence

ORD record: ord-82daf88a96e44977936b7fa619e59141
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138197B2

Reaction notes

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