Hydrochloric Acid → HCID 67539196, compound

HRID 1192409Notes

Reaction equation

HRID 1192409 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:15]3[CH2:23][CH2:22][C@H:21]([CH3:24])[N:20](C(=O)C(OC)(C4C=CC=CC=4)C(F)(F)F)[C:16]=3[N:17]=[CH:18][N:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-].Cl>CO>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[C:15]3[CH2:23][CH2:22][C@H:21]([CH3:24])[NH:20][C:16]=3[N:17]=[CH:18][N:19]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67539629HCID 67539629, compound

Product 1

HCID 67539196HCID 67539196, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (7S)-4-[7-Methyl-8-(3,3,3-trifluoro-2-methoxy-2-phenyl-propionyl)-5,6,7,8-tetrahydro-pyrido[2,3-d]pyrimidin-4-yl]-piperazine-1-carboxylic acid tert-butyl ester (84 mg, 0.153 mmol) in MeOH (5 mL) was added LiOH (3M, 4 mL). The mixture was stirred at room temperature for 4 days and then neutralized with 2N HCl. The solvent was removed and the residue was subject to column chromatography, eluted by ethyl acetate—DCM/MeOH (20:1) to afford (7S)-4-(7-Methyl-5,6,7,8-tetrahydro-pyrido[2,3-d]pyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester (32 mg, 63%). 1H NMR (CDCl3, 400 MHz) δ 8.11 (s, 1H), 5.20 (s, 1H), 3.54 (m, 5H), 3.30 (m, 4H), 2.57 (m, 2H), 1.95 (m, 1H), 1.48 (s, 9H), 1.40 (m, 1H), 1.27 (d, J=6.4 Hz, 3H). MS (APCI+) [M+H]+334.

Workup

  1. customThe solvent was removed
  2. washeluted by ethyl acetate—DCM/MeOH (20:1)

Sources & evidence

ORD record
ord-8b3185c3b58a4ee1bb0011512d36fd0d
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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