Hydrochloric Acid → HCID 67996739, compound

HRID 1467336Notes

Reaction equation

HRID 1467336 reaction equation
[Li+].[OH-].[F:3][C:4]1[CH:39]=[CH:38][CH:37]=[C:36]([O:40][CH3:41])[C:5]=1[CH2:6][N:7]1[CH2:12][C@H:11]([NH:13][C:14]([C:16]2[CH:17]=[C:18]3[C:22](=[CH:23][CH:24]=2)[NH:21][N:20]=[C:19]3[C:25]2[CH:30]=[CH:29][N:28]=[C:27]([CH3:31])[CH:26]=2)=[O:15])[CH2:10][CH2:9][C@H:8]1[C:32]([O:34]C)=[O:33].Cl>C1COCC1.CO.CCOCC>[F:3][C:4]1[CH:39]=[CH:38][CH:37]=[C:36]([O:40][CH3:41])[C:5]=1[CH2:6][N:7]1[CH2:12][C@H:11]([NH:13][C:14]([C:16]2[CH:17]=[C:18]3[C:22](=[CH:23][CH:24]=2)[NH:21][N:20]=[C:19]3[C:25]2[CH:30]=[CH:29][N:28]=[C:27]([CH3:31])[CH:26]=2)=[O:15])[CH2:10][CH2:9][C@H:8]1[C:32]([OH:34])=[O:33]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium Hydroxide2×HCID 86681281HCID 86681281, compound

Product 1

HCID 67996739HCID 67996739, compoundYield 68.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

LiOH (1M, aqueous) (3.0 ml, 3.00 mmol) was added to a stirred mixture of (2S,5R)-methyl 1-(2-fluoro-6-methoxybenzyl)-5-(3-(2-methylpyridin-4-yl)-1H-indazole-5-carboxamido)piperidine-2-carboxylate (1 g, 1.881 mmol) in THF (30 ml) & MeOH (10 ml) and the mixture was stirred at room temperature for Overnight. The reaction LCMS showed most starting material (M+1=532), but tlc showed product, another 3 ml of LiOH was added to the r×n, stirred for one day, LCMS gave M+H at 518, tlc showed completion. The reaction was treated 1 N HCl in ether, 6 ml, 1 eq, and rotovap to dryness and the residue was purified by column chromatography on silica gel Biotage 40M, eluting with 20% MeOH/CH2Cl2 to give the titled compound as a off-white (0.67 g, 68.8% yield).

Workup

  1. customThe reaction LCMS
  2. stirringstirred for one day
  3. customLCMS gave M+H at 518, tlc
  4. customthe residue was purified by column chromatography on silica gel Biotage 40M
  5. washeluting with 20% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-75fdcbf7899742b8847411b98fbbaeac
Source dataset
uspto-grants-2015_04
Patent number
US08999957B2

Reaction notes

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