Hydrochloric Acid → HCID 86652653, compound

HRID 43013Notes

Reaction equation

HRID 43013 reaction equation
O.C(OC([NH:12][C@@H:13]1[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([CH2:22][N:23]3[C:27]([C:28]([F:31])([F:30])[F:29])=[C:26]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:25]=[N:24]3)[CH:19]=2)[CH2:14]1)=O)C1C=CC=CC=1.C(Cl)[Cl:38].Cl>C(O)C.[OH-].[Pd+2].[OH-]>[ClH:38].[NH2:12][C@@H:13]1[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([CH2:22][N:23]3[C:27]([C:28]([F:29])([F:30])[F:31])=[C:26]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:25]=[N:24]3)[CH:19]=2)[CH2:14]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6344DichloromethaneHCID 70244523(S)-Ethyl 1-((2-(benzyloxycarbonylamino)-2,3-dihydro-1H-inden-5-yl)methyl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate

Product 1

HCID 86652653HCID 86652653, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

Palladium hydroxide (0.092 mmol, 12.96 mg) was wetted with a small volume of water before addition of (S)-ethyl 1-((2-(benzyloxycarbonylamino)-2,3-dihydro-1H-inden-5-yl)methyl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate (0.092 mmol, 45 mg) in Ethanol (5 mL). A small volume DCM was added to aid solubility. Aq. HCl 5N (0.500 ml) was added before the mixture was left to stand at room temp for around 1.5 h before hydrogenating at 2 bar for 45 min. After this time, the mixture was filtered through a filter tip and concentrated to give the desired product as a colourless oil (36 mg, 0.092 mmol, 100%). 1H NMR (400 MHz, CD3OD) δ 1.33 (t, 3H) 2.98 (m, 2H) 3.40 (m, 2H) 4.10 (m, 1H) 4.31 (q, 2H) 5.50 (s, 2H) 7.05 (d, 1H), 7.10 (s, 1H), 7.27 (d, 1H) 8.04 (s, 1H).

Workup

  1. waitwas left
  2. filtrationAfter this time, the mixture was filtered through a filter tip
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-a8d631486d634232bf1f7ef51d573030
Source dataset
uspto-grants-2013_09
Patent number
US08536214B2

Reaction notes

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