Potassium Hydroxide → HCID 178424013, compound

HRID 2174024Notes

Reaction equation

HRID 2174024 reaction equation
[OH:1][C:2]1([C:26]2[NH:30][C:29]3[CH:31]=[CH:32][C:33]([C:35]#[N:36])=[CH:34][C:28]=3[N:27]=2)[C:12]2[C:13]3[C:5](=[CH:6][N:7](S(C4C=CC(C)=CC=4)(=O)=O)[C:8]=3[C:9]([CH3:15])=[CH:10][C:11]=2[CH3:14])[CH2:4][CH2:3]1.CCN(CCOC(C1(CCC(C)C)CCCCC1)=O)CC.[OH-].[K+]>CCO>[OH:1][C:2]1([C:26]2[NH:30][C:29]3[CH:31]=[CH:32][C:33]([C:35]#[N:36])=[CH:34][C:28]=3[N:27]=2)[C:12]2[C:13]3[C:5](=[CH:6][NH:7][C:8]=3[C:9]([CH3:15])=[CH:10][C:11]=2[CH3:14])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 14797Potassium Hydroxide2×HCID 28221Isomylamine2×HCID 178427311HCID 178427311, compound

Product 1

HCID 178424013HCID 178424013, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

(±)-2-(5-Hydroxy-6,8-dimethyl-1-tosyl-1,3,4,5-tetrahydrobenzo[cd]indol-5-yl)-1H-benzo[d]imidazole-5-carbonitrile (41 mg, 0.083 mmol) in EtOH (0.83 mL) was treated with isomylamine (190 μL, 1.65 mmol) and KOH (46.3 mg, 0.826 mmol) and heated in a microwave for 30 minutes at 100° C. After 30 minutes an additional aliquot of isomylamine (190 μL, 1.65 mmol) and KOH (46.3 mg, 0.826 mmol) were added and the reaction heated in a microwave. After 30 minutes the reaction was complete. It was directly loaded onto a column and purified using FCC eluting with heptane:EtOAc 1:2 to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ 12.79 (s, 1H), 10.59 (br. s., 1H), 7.89-7.95 (m, 1H), 7.55-7.72 (m, 1H), 7.34-7.55 (m, 1H), 7.01 (s, 1H), 6.56 (s, 1H), 6.15 (m, 1H), 2.89-2.90 (m, 2H), 2.27-2.45 (m, 5H). HRMS calcd. for C21H18N4O (M+H)+ 343.1554. found 343.156.

Workup

  1. temperaturethe reaction heated in a microwave
  2. custompurified
  3. washeluting with heptane:EtOAc 1:2

Sources & evidence

ORD record
ord-3d048ac8bf414522a9a72001c743577f
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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