HCID 178418361, compound → HCID 178521732, compound

HRID 1028221Notes

Reaction equation

HRID 1028221 reaction equation
COC1C=CC(C[N:8]2[N:12]=[N:11][C:10]([CH2:13][C@H:14]3[CH2:19][CH2:18][C@H:17]([O:20][C:21]([N:23]4[CH2:32][CH2:31][C:30]5[C:25](=[CH:26][CH:27]=[C:28]([NH:33][C:34]([NH:36][C:37]6[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=6[F:43])=[O:35])[CH:29]=5)[CH2:24]4)=[O:22])[CH2:16][CH2:15]3)=[N:9]2)=CC=1.[H][H]>[C].[Pd].C(O)C>[N:11]1[NH:12][N:8]=[N:9][C:10]=1[CH2:13][C@H:14]1[CH2:19][CH2:18][C@H:17]([O:20][C:21]([N:23]2[CH2:32][CH2:31][C:30]3[C:25](=[CH:26][CH:27]=[C:28]([NH:33][C:34]([NH:36][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=4[F:43])=[O:35])[CH:29]=3)[CH2:24]2)=[O:22])[CH2:16][CH2:15]1

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178490922HCID 178490922, compound

Product 1

HCID 178521732HCID 178521732, compoundYield 8.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

An ethanol (6 mL) suspension of trans-6-[3-(2-fluoro-phenyl)-ureido]-3,4-dihydro-1H-isoquinoline-2-carboxylic acid 4-[2-(4-methoxy-benzyl)-2H-tetrazol-5-ylmethyl]-cyclohexyl ester (333 mg) obtained in Example (44e) and palladium carbon (55 mg) was stirred at room temperature for 3 days in a hydrogen atmosphere. The reaction mixture was filtered through Celite and concentrated. The residue was purified by column chromatography (dichloromethane/ethyl acetate=5:1→1:1 and then dichloromethane/methanol=25:1→5:1) to obtain the title compound (22 mg, 8%) as an off-white solid.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationconcentrated
  3. customThe residue was purified by column chromatography (dichloromethane/ethyl acetate=5:1→1:1

Sources & evidence

ORD record
ord-1c3bba0ccccf46cb8aeceae714831791
Source dataset
uspto-grants-2014_05
Patent number
US08735425B2

Reaction notes

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