Ethyl Acetate → HCID 178429376, compound

HRID 707311Notes

Reaction equation

HRID 707311 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C@H:11]1[CH2:14][C@H:13]([NH:15][C:16]2[C:17]([C:22]([CH3:26])([CH3:25])[C:23]#N)=[N:18][CH:19]=[CH:20][N:21]=2)[CH2:12]1.C(OCC)(=[O:29])C.[OH-].[Na+]>O.S(=O)(=O)(O)O>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C@H:11]1[CH2:12][C@H:13]([N:15]2[C:16]3=[N:21][CH:20]=[CH:19][N:18]=[C:17]3[C:22]([CH3:26])([CH3:25])[C:23]2=[O:29])[CH2:14]1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 178448868HCID 178448868, compound

Product 1

HCID 178429376HCID 178429376, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
100 °C

Procedure

2-(3-((Trans-3-(benzo[d]thiazol-2-ylamino)cyclobutyl)amino)pyrazin-2-yl)-2-methylpropanenitrile (0.067 g, 0.184 mmol) was dissolved in a mixture of water (3 mL) and concentrated sulfuric acid (2 mL) and heated at 100° C. After 35 minutes the heat was turned off and the reaction allowed to cool in the oil bath over 90 minutes. Water (100 mL), ice (about 100 mL), and ethyl acetate (200 mL) were added followed by 5 N sodium hydroxide (15 mL). The phases were mixed and separated and the organic dried with magnesium sulfate before evaporating to dryness under reduced pressure. Purification using silica chromatography (dichloromethane to ethyl acetate gradient) gave the desired 5-(trans-3-(benzo[d]thiazol-2-ylamino)cyclobutyl)-7,7-dimethyl-5H-pyrrolo[2,3-b]pyrazin-6(7H)-one (0.061 g, 0.167 mmol, 91% yield) as a white solid. M+1: 366.2. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.45 (s, 6 H) 2.42-2.58 (m, 2 H) 3.45 (s, 2 H) 4.53-4.68 (m, 1 H) 5.31 (quin, J=8.46 Hz, 1 H) 6.53 (br. s, 1 H) 7.04-7.15 (m, 1 H) 7.30 (t, J=7.24 Hz, 1 H) 7.59 (d, J=8.22 Hz, 1 H) 7.61 (d, J=8.02 Hz, 1 H) 8.09 (d, J=3.33 Hz, 1 H) 8.13 (d, J=3.30 Hz, 1 H).

Workup

  1. temperatureto cool in the oil bath over 90 minutes
  2. additionThe phases were mixed
  3. customseparated
  4. dry with materialthe organic dried with magnesium sulfate
  5. custombefore evaporating to dryness under reduced pressure
  6. customPurification

Sources & evidence

ORD record
ord-92424de41f744c449c47c9bc751ffb51
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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