Water → HCID 86717560, compound

HRID 712109Notes

Reaction equation

HRID 712109 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:15]1([CH2:25][OH:26])[CH2:24][CH2:23][C:18]2([O:22][CH2:21][CH2:20][O:19]2)[CH2:17][CH2:16]1.C(N(CC)CC)C.O>C(O)(C)C>[N+:8]([C:7]1[C:2]([NH:14][C:15]2([CH2:25][OH:26])[CH2:24][CH2:23][C:18]3([O:19][CH2:20][CH2:21][O:22]3)[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

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 142079507-Chloro-6-nitrothieno[3,2-b]pyridineHCID 840719951607592-18-6

Product 1

HCID 86717560HCID 86717560, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 7-chloro-6-nitrothieno[3,2-b]pyridine (229 mg, 1.07 mmol), (8-amino-1,4-dioxaspiro[4.5]dec-8-yl)methanol (240 mg, 1.28 mmol) and triethylamine (300 μL, 2 mmol) in isopropyl alcohol (3.5 mL) was stirred at 90° C. overnight. After cooling to room temperature, water was added, which caused more solids to form. The solids were filtered, washed with water, and dried to give 219 mg (56%) of the desired product. LCMS calculated for C16H20N3O5S (M+H)+: m/z=366.1. Found: 366.1. 1H NMR (300 MHz, CDCl3) δ 8.93 (s, 1H), 7.78-7.75 (m, 2H), 4.17 (s, 2H), 4.02-3.84 (m, 4H), 2.52 (d, J=13.3 Hz, 2H), 2.12-1.82 (m, 4H), 1.78-1.44 (m, 4H) ppm.

Workup

  1. temperatureAfter cooling to room temperature
  2. customto form
  3. filtrationThe solids were filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-9c6c4318895f4399b51b1e73f7d1b29e
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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