Acetic Acid → HCID 86717510, compound

HRID 712054Notes

Reaction equation

HRID 712054 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])[C@H:14]([O:21][CH3:22])[CH2:13]2)=[C:4]2[S:10][CH:9]=[CH:8][C:5]2=[N:6][CH:7]=1.[C:23](OCC)(OCC)(OCC)[CH3:24].C(O)(=O)C>>[CH3:22][O:21][C@@H:14]1[CH2:13][C@@H:12]([N:11]2[C:3]3=[C:4]4[S:10][CH:9]=[CH:8][C:5]4=[N:6][CH:7]=[C:2]3[N:1]=[C:23]2[CH3:24])[CH2:17][CH2:16][C@@H:15]1[CH2:18][C:19]#[N:20]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 66221Triethyl orthoacetateHCID 86717509HCID 86717509, compound

Product 1

HCID 86717510HCID 86717510, compoundYield 58.7%

Conditions

Temperature
120 °C

Procedure

A mixture of {(1R,2R,4S)-4-[(6-aminothieno[3,2-b]pyridin-7-yl)amino]-2-methoxycyclohexyl}acetonitrile (racemic) (45 mg, 0.14 mmol) and triethyl orthoacetate (79 μL, 0.43 mmol) in acetic acid (0.4 mL, 7 mmol) was stirred at 120° C. for 30 min. The solvent was removed, and the residue dissolved in 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 60 mL/min) to give the desired product (28 mg, 58%). LCMS calculated for C18H21N4OS (M+H)+: m/z=341.1. Found: 341.0.

Workup

  1. customThe solvent was removed
  2. dissolutionthe residue dissolved in methanol
  3. custompurified with prep-LCMS (XBridge C18 column
  4. washeluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 60 mL/min)

Sources & evidence

ORD record
ord-ac7b89950e474e1e91fc762195ca1f4a
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

Loading…