Hydrochloric Acid → HCID 58208693, compound

HRID 38460Notes

Reaction equation

HRID 38460 reaction equation
[OH-].[Na+].[CH:3]1([N:6]2[C:14]3[C:9](=[C:10]([N:39]4[CH2:44][CH2:43][CH:42]([C:45]([O:47]CC)=[O:46])[CH2:41][CH2:40]4)[CH:11]=[C:12]([C:15]([N:17]4[CH2:22][CH2:21][C:20]5([CH2:31][C:30](=[O:32])[C:29]6[C:24](=[CH:25][CH:26]=[C:27]([C:33]7[CH:34]=[N:35][N:36]([CH3:38])[CH:37]=7)[CH:28]=6)[O:23]5)[CH2:19][CH2:18]4)=[O:16])[CH:13]=3)[CH:8]=[CH:7]2)[CH2:5][CH2:4]1.CO.Cl>C1COCC1>[CH:3]1([N:6]2[C:14]3[C:9](=[C:10]([N:39]4[CH2:44][CH2:43][CH:42]([C:45]([OH:47])=[O:46])[CH2:41][CH2:40]4)[CH:11]=[C:12]([C:15]([N:17]4[CH2:18][CH2:19][C:20]5([CH2:31][C:30](=[O:32])[C:29]6[C:24](=[CH:25][CH:26]=[C:27]([C:33]7[CH:34]=[N:35][N:36]([CH3:38])[CH:37]=7)[CH:28]=6)[O:23]5)[CH2:21][CH2:22]4)=[O:16])[CH:13]=3)[CH:8]=[CH:7]2)[CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 67055569HCID 67055569, compound

Product 1

HCID 58208693HCID 58208693, compoundYield 35.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Aqueous 1N NaOH (0.409 ml, 0.409 mmol) was added to a stirred solution of ethyl 1-(1-cyclopropyl-6-{[6-(1-methyl-1H-pyrazol-4-yl)-4-oxospiro[chroman-2,4′-piperidin]-1′-yl]carbonyl}-1H-indol-4-yl)piperidine-4-carboxylate in THF (1 ml)-MeOH (1 ml) and the mixture was stirred at room temperature overnight. Aqueous 1N HCl (0.409 ml) was added to the mixture and the solvent was evaporated under reduced pressure. The residue was suspended in CHCl3-MeOH (8:2) and the mixture stirred for 1 h. at room temperature. The insoluble material was filtered off and the filtrate was concentrated in vacuo. The crude material was purified by preparative HPLC (ODS, 0.1% HCOOH in H2O/MeCN, gradient) to give intended compound (44.4 mg, 0.073 mmol, 35.7% yield) as a pale orange solid.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. stirringthe mixture stirred for 1 h. at room temperature
  3. filtrationThe insoluble material was filtered off
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe crude material was purified by preparative HPLC (ODS, 0.1% HCOOH in H2O/MeCN, gradient)

Sources & evidence

ORD record
ord-cf45da34016d4edbb10544e909874f11
Source dataset
uspto-grants-2013_09
Patent number
US08524730B2

Reaction notes

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