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1-Hydroxybenzotriazole → HCID 24965744, compound

HRID 420128
Notes
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Reaction equation

HRID 420128 reaction equation
[C:1]([C:4]1[C:12]2[C:7](=[CH:8][C:9]([C:16](O)=[O:17])=[CH:10][C:11]=2[O:13][CH2:14][CH3:15])[N:6]([CH:19]2[CH2:21][CH2:20]2)[CH:5]=1)(=[O:3])[NH2:2].Cl.[CH3:23][O:24][C:25](=[O:48])[C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:32]2[CH:33]=[C:34]3[C:44](=[CH:45][CH:46]=2)[O:43][C:37]2([CH2:42][CH2:41][NH:40][CH2:39][CH2:38]2)[CH2:36][C:35]3=[O:47])[CH:27]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.C(OCC)(=O)C.C(N(CC)CC)C>[C:1]([C:4]1[C:12]2[C:7](=[CH:8][C:9]([C:16]([N:40]3[CH2:39][CH2:38][C:37]4([CH2:36][C:35](=[O:47])[C:34]5[C:44](=[CH:45][CH:46]=[C:32]([C:28]6[CH:27]=[C:26]([CH:31]=[CH:30][CH:29]=6)[C:25]([O:24][CH3:23])=[O:48])[CH:33]=5)[O:43]4)[CH2:42][CH2:41]3)=[O:17])=[CH:10][C:11]=2[O:13][CH2:14][CH3:15])[N:6]([CH:19]2[CH2:21][CH2:20]2)[CH:5]=1)(=[O:3])[NH2:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66649548HCID 66649548, compoundHCID 66649562HCID 66649562, compound

Product 1

HCID 24965744HCID 24965744, compound

Reagents, catalysts & solvents 3

HCID 6228
Dimethylformamide
Solvent
HCID 8471TriethylamineSolvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Triethylamine (0.22 mL) was added to a solution of 3-carbamoyl-1-cyclopropyl-4-ethoxy-1H-indole-6-carboxylic acid (229 mg), 3-(4-oxo-spiro[chroman-2,4′-piperidin]-6-yl)benzoic acid methyl ester hydrochloride (306 mg), WSC hydrochloride (166 mg) and HOBT (133 mg) in DMF (4 mL), and the mixture was stirred at 60° C. for 1 hour. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate, then washed successively with water, aqueous saturated sodium bicarbonate and saturated saline water. The organic layer was dried over sodium sulfate, filtered, concentrated, and purified through silica gel column chromatography (chloroform/methanol) to obtain the intended ester derivative as a colorless amorphous substance. 1H-NMR (400 MHz, CDCl3) δ: 8.71 (1H, s), 8.25 (1H, dd, J=1.5, 1.5 Hz), 8.14 (1H, d, J=2.4 Hz), 8.04-8.00 (2H, m), 7.83-7.74 (2H, m), 7.51 (1H, dd, J=7.8, 7.8 Hz), 7.37 (1H, d, J=1.5 Hz), 7.13 (1H, d, J=7.8 Hz), 6.74 (1H, d, J=1.5 Hz), 5.54 (1H, s), 4.62-4.41 (1H, br m), 4.29 (2H, q, J=7.0 Hz), 3.95 (3H, s), 2.28-1.71 (4H, br m), 3.88-3.32 (4H, br m), 2.82 (2H, s), 1.55 (3H, t, J=7.0 Hz), 1.16-1.00 (4H, m); MS [M+H]+=622.

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed successively with water, aqueous saturated sodium bicarbonate and saturated saline water
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified through silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-a07f7ad9c8d549d69cee97eeba63d14c
Source dataset
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08093389B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes