Diisopropylethylamine → HCID 178526780, compound

HRID 711932Notes

Reaction equation

HRID 711932 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]2[CH:11]=[CH:12][S:13][C:3]=12.[NH2:14][C@H:15]1[CH2:20][CH2:19][C@H:18]([CH2:21][OH:22])[CH2:17][CH2:16]1.C(N(CC)C(C)C)(C)C>C(O)(C)C>[N+:8]([C:7]1[C:2]([NH:14][C@H:15]2[CH2:20][CH2:19][C@H:18]([CH2:21][OH:22])[CH2:17][CH2:16]2)=[C:3]2[S:13][CH:12]=[CH:11][C:4]2=[N:5][CH:6]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 142079507-Chloro-6-nitrothieno[3,2-b]pyridineHCID 178511560HCID 178511560, compound

Product 1

HCID 178526780HCID 178526780, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 7-chloro-6-nitrothieno[3,2-b]pyridine (0.21 g, 0.98 mmol) (Example 1, Step 2), (trans-4-aminocyclohexyl)methanol (from J&W Pharmatech, 0.25 g, 2.0 mmol) and N,N-diisopropylethylamine (0.51 mL, 2.9 mmol) in isopropyl alcohol (3.3 mL) was heated at 90° C. for 2 h. The resulting mixture was concentrated and purified on silica gel (eluting with 0 to 60% EtOAc in hexanes) to give the desired product (0.26 g, 86%). LCMS calculated for C14H18N3O3S (M+H)+: m/z=308.1. Found: 308.0.

Workup

  1. concentrationThe resulting mixture was concentrated
  2. custompurified on silica gel (eluting with 0 to 60% EtOAc in hexanes)

Sources & evidence

ORD record
ord-cb2e8c2f07264c0cb7f7a6a54d5d31ba
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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