Sodium Hydroxide → HCID 11418548, compound

HRID 2373912Notes

Reaction equation

HRID 2373912 reaction equation
C[O:2][C:3](=[O:32])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]3[N:19]=[C:20]([CH:28]4[CH2:31][CH2:30][CH2:29]4)[N:21]4[CH:26]=[CH:25][N:24]=[C:23]([NH2:27])[C:22]=34)[CH:13]=2)[CH:5]=1.[OH-].[Na+]>C1COCC1>[NH2:27][C:23]1[C:22]2[N:21]([C:20]([CH:28]3[CH2:31][CH2:30][CH2:29]3)=[N:19][C:18]=2[C:14]2[CH:13]=[C:12]([CH:17]=[CH:16][CH:15]=2)[O:11][CH2:10][C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=2)[C:3]([OH:32])=[O:2])[CH:26]=[CH:25][N:24]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11774683HCID 11774683, compound

Product 1

HCID 11418548HCID 11418548, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A 5 mL methanolic solution of 3-[3-(8-Amino-3-cyclobutyl-imidazo[1,5-a]pyrazin-1-yl)-phenoxymethyl]-benzoic acid methyl ester (600 mg, 1.40 mmol) with 5 mL THF was charged with 5 mL of 10 N NaOH and the reaction mixture was heated to 60° C. After 1 h, the reaction was allowed to cool to rt and the pH of the reaction mixture was lowered to 3-4. A white precipitate formed, which was filtered and washed with hexanes to afford the title compound as a white powder; 1H NMR (CDCl3, 400 MHz) δ 1.90-1.97 (m, 1H), 2.04-2.15 (m, 1H), 2.36-2.56 (m, 4H), 3.60-3.79 (m, 1H), 5.10 (s, 2H), 6.84 (d, J=5.2 Hz, 1H), 6.97-7.01 (m, 1H), 7.07 (d, J=5.6 Hz, 1H), 7.12-7.15 (m, 2H), 7.32-7.40 (m, 2H), 7.54 (d, J=7.2 Hz, 1H), 7.91 (d, J=7.6 Hz, 1H), 8.02 (s, 1H); MS (ES+): m/z 415.15 (100) [MH+].

Workup

  1. temperatureto cool to rt
  2. customA white precipitate formed
  3. filtrationwhich was filtered
  4. washwashed with hexanes

Sources & evidence

ORD record
ord-61569eea461e4a2ea58b406c4270607c
Source dataset
uspto-grants-2008_12
Patent number
US07459554B2

Reaction notes

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