Hydrochloric Acid → 3-(1'-{[1-Cyclopropyl-4-(tetrazol-5-yl)-1H-indol-6-yl]carbonyl}-4-oxospiro[chroman-2,4'-piperidin]-6-yl)benzamide

HRID 1096909Notes

Reaction equation

HRID 1096909 reaction equation
Cl.[O:2]=[C:3]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:18]3[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=3)[C:21]([NH2:23])=[O:22])[CH:16]=2)[O:11][C:5]2([CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[CH2:4]1.[CH:27]1([N:30]2[C:38]3[C:33](=[C:34]([C:42]4[NH:46][N:45]=[N:44][N:43]=4)[CH:35]=[C:36]([C:39](O)=[O:40])[CH:37]=3)[CH:32]=[CH:31]2)[CH2:29][CH2:28]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.Cl>CN(C=O)C.O.C(N(CC)CC)C>[CH:27]1([N:30]2[C:38]3[C:33](=[C:34]([C:42]4[NH:46][N:45]=[N:44][N:43]=4)[CH:35]=[C:36]([C:39]([N:8]4[CH2:7][CH2:6][C:5]5([CH2:4][C:3](=[O:2])[C:17]6[C:12](=[CH:13][CH:14]=[C:15]([C:18]7[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=7)[C:21]([NH2:23])=[O:22])[CH:16]=6)[O:11]5)[CH2:10][CH2:9]4)=[O:40])[CH:37]=3)[CH:32]=[CH:31]2)[CH2:28][CH2:29]1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 667824533-(4-Oxospiro[chroman-2,4'-piperidin]-6-yl)benzamide hydrochlorideHCID 178524187HCID 178524187, compound

Product 1

HCID 1785136303-(1'-{[1-Cyclopropyl-4-(tetrazol-5-yl)-1H-indol-6-yl]carbonyl}-4-oxospiro[chroman-2,4'-piperidin]-6-yl)benzamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
50 °C

Procedure

3-(4-Oxospiro[chroman-2,4′-piperidin]-6-yl)benzamide hydrochloride (224 mg), 1-cyclopropyl-4-(tetrazol-5-yl)-1H-indole-6-carboxylic acid (135 mg), EDCI (115 mg), HOBT (91.2 mg) and triethylamine (0.209 ml) were dissolved in DMF (3 mL), and stirred at 50° C. for 23 hours. 1N hydrochloric acid and water were added to the reaction liquid, the formed solid was taken out through filtration, and the resulting solid was purified through silica gel thin-layer column chromatography (chloroform/methanol) to obtain the title compound. 1H-NMR (400 MHz, DMSO-d6) δ: 8.17-8.10 (2.0H, br m), 8.05 (1.0H, d, J=2.2 Hz), 7.99 (1.0H, dd, J=8.5, 2.2 Hz), 7.86-7.78 (4.0H, m), 7.63 (1.0H, d, J=2.9 Hz), 7.52 (1.0H, dd, J=7.7, 7.7 Hz), 7.40 (1.0H, s), 7.25 (1.0H, d, J=8.5 Hz), 7.15-7.13 (1.0H, m), 4.50-4.08 (1.0H, br m), 3.88-3.08 (4.0H, m), 2.96 (2.0H, s), 2.23-1.68 (4.0H, m), 1.15-1.08 (2.0H, m), 1.06-0.96 (2.0H, m). MS [M+H]+=588.

Workup

  1. filtrationthe formed solid was taken out through filtration
  2. customthe resulting solid was purified through silica gel thin-layer column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-9f670a464cca4ef68df9f28bab3f4bdc
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

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