Tetrahydrofuran → HCID 12087763, compound

HRID 719762Notes

Reaction equation

HRID 719762 reaction equation
O1CCCC1.[NH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][C:14]23[CH2:23][CH:18]4[CH2:19][CH:20]([CH2:22][CH:16]([CH2:17]4)[CH2:15]2)[CH2:21]3)=[N:11][CH:12]=1.C(N(CC)CC)C.[Cl:31][C:32]1[CH:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[CH:37][C:33]=1[C:34](Cl)=[O:35]>O>[C:14]12([O:13][C:10]3[CH:9]=[CH:8][C:7]([NH:6][C:34](=[O:35])[C:33]4[CH:37]=[C:38]([N+:41]([O-:43])=[O:42])[CH:39]=[CH:40][C:32]=4[Cl:31])=[CH:12][N:11]=3)[CH2:15][CH:16]3[CH2:22][CH:20]([CH2:19][CH:18]([CH2:17]3)[CH2:23]1)[CH2:21]2

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 117637Benzoyl chloride, 2-chloro-5-nitro-HCID 21901884HCID 21901884, compound

Product 1

HCID 12087763HCID 12087763, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 5 mL of a tetrahydrofuran solution comprising 290 mg of 5-amino-2-(1-adamantyloxy)pyridine) and 150 mg of triethylamine, 5 mL of a tetrahydrofuran solution comprising 260 mg of 2-chloro-5-nitrobenzoylchloride was dropwise added, followed by stirring for about 30 minutes, and then water was added, and the precipitated crystals were collected by filtration. The collected crystals were washed with water and then dried to obtain 330 mg of N-(2-(1-adamantyloxy)-5-pyridyl)-2-chloro-5-nitrobenzamide (Compound No. 123) having a melting point of from 98 to 105° C.

Workup

  1. additionwas dropwise added
  2. filtrationthe precipitated crystals were collected by filtration
  3. washThe collected crystals were washed with water
  4. customdried

Sources & evidence

ORD record
ord-ab51e396def64055a1d55aae6b357ddd
Source dataset
uspto-grants-2006_11
Patent number
US07132546B2

Reaction notes

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