Hydrochloric Acid → HCID 178520087, compound

HRID 1257762Notes

Reaction equation

HRID 1257762 reaction equation
C1(S([N:10]2[CH:21]=[CH:20][C:19]3[C:11]2=[N:12][CH:13]=[C:14]2[C:18]=3[N:17]([CH:22]3[CH2:27][CH2:26][C:25]([CH2:29][OH:30])([OH:28])[CH2:24][CH2:23]3)[N:16]=[N:15]2)(=O)=O)C=CC=CC=1.[OH-].[Na+].Cl>CO.O>[OH:30][CH2:29][C:25]1([OH:28])[CH2:24][CH2:23][CH:22]([N:17]2[C:18]3[C:14](=[CH:13][N:12]=[C:11]4[C:19]=3[CH:20]=[CH:21][NH:10]4)[N:15]=[N:16]2)[CH2:27][CH2:26]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67345773HCID 67345773, compound

Product 1

HCID 178520087HCID 178520087, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-(6-Benzenesulfonyl-6H-1,2,3,5,6-pentaaza-as-indacen-1-yl)-1-hydroxymethyl-cyclohexanol (200 mg, 0.47 mmol) in methanol (25 mL) was added a solution of sodium hydroxide (46.8 mg, 1.17 mmol) in water (5 mL), then the reaction mixture was stirred at 60° C. for 3 hours and neutralized with dilute hydrochloride acid until pH=7. The reaction mixture was purified by a reverse-phase preparatory HPLC (Column: Waters Xbridge C18 150*30 mm*5 um, 0% to 25%: acetonitrile+0.05% NH4OH in water, 10 min, 25 mL/min) to give 15.9 mg (39%) of 1-Hydroxymethyl-4-(6H-1,2,3,5,6-pentaaza-as-indacen-1-yl)-cyclohexanol, LCMS (Method K, ESI): RT=0.873 min, m+H=288.0; 1H NMR (400 MHz, DMSO-d6) δ: 8.97 (s, 1H), 7.57 (d, 1H), 6.96 (d, 1H), 5.14-5.07 (m, 1H), 4.62-4.57 (m, 1H), 4.31-4.25 (m, 1H), 3.52 (s, 3H), 2.25-2.18 (m, 2H), 2.18-2.15 (m, 2H), 1.93-1.90 (m, 2H), 1.62-1.51 (m, 2H); and 19.3 mg (39%) of 1-Hydroxymethyl-4-(6H-1,2,3,5,6-pentaaza-as-indacen-1-yl)-cyclohexanol, LCMS (Method K, ESI): RT=0.889 min, m+H=288.1; 1H NMR (400 MHz, DMSO-d6) δ: 12.32 (s, 1H), 8.96 (s, 1H), 7.57 (s, 1H), 7.17 (s, 1H), 5.01-4.98 (m, 1H), 4.67 (d, 1H), 4.38 (d, 2H), 2.54-2.46 (m, 2H), 1.88-1.63 (m, 6H).

Workup

  1. customThe reaction mixture was purified by a reverse-phase preparatory HPLC (Column: Waters Xbridge C18 150*30 mm*5 um, 0% to 25%: acetonitrile+0.05% NH4OH in water, 10 min, 25 mL/min)

Sources & evidence

ORD record
ord-7a973d9ac87d4def88c6c1d4766835f2
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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