Ethyl orthopropionate → HCID 178437531, compound

HRID 712078Notes

Reaction equation

HRID 712078 reaction equation
[NH2:1][C:2]1[C:3]([NH:11][C@H:12]2[CH2:17][CH2:16][C@H:15]([CH2:18][C:19]#[N:20])[CH2:14][CH2:13]2)=[C:4]2[S:10][CH:9]=[CH:8][C:5]2=[N:6][CH:7]=1.C(O[C:24](OCC)(OCC)[CH2:25][CH3:26])C>C(O)(=O)C.CO>[CH2:25]([C:26]1[N:11]([C@H:12]2[CH2:13][CH2:14][C@H:15]([CH2:18][C:19]#[N:20])[CH2:16][CH2:17]2)[C:3]2=[C:4]3[S:10][CH:9]=[CH:8][C:5]3=[N:6][CH:7]=[C:2]2[N:1]=1)[CH3:24]

Participants

5

Reactant 2

HCID 66995Ethyl orthopropionateHCID 178511084HCID 178511084, compound

Product 1

HCID 178437531HCID 178437531, compoundYield 57.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of {trans-4-[(6-aminothieno[3,2-b]pyridin-7-yl)amino]cyclohexyl}acetonitrile (20.1 mg, 0.0702 mmol) and 1,1,1-triethoxypropane (0.0428 mL, 0.213 mmol) in acetic acid (0.2 mL) was stirred at 120° C. for 30 min. The mixture was diluted with methanol and purified with prep-LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 30 mL/min) to give the desired product (13 mg, 57%). LCMS calculated for C18H21N4S (M+H)+: m/z=325.1. Found: 325.1.

Workup

  1. custompurified with prep-LCMS (XBridge C18 column
  2. washeluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 30 mL/min)

Sources & evidence

ORD record
ord-c9e9683c77b741d1a559fd26b41b6e2a
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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