Triethylamine → HCID 9966285, compound

HRID 432613Notes

Reaction equation

HRID 432613 reaction equation
[CH:1]1([C:4](O)=O)C[CH2:2]1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:14])C=CC=CC=1.C([N:26]([CH2:29]C)CC)C.[NH2:31][C:32]1[C:33]([OH:43])=[C:34]([S:39]([NH2:42])(=[O:41])=[O:40])[C:35]([Cl:38])=[CH:36][CH:37]=1>CN(C)C=O>[NH2:42][S:39]([C:34]1[C:33]([OH:43])=[C:32]([NH:31][C:29]([NH:26][CH:4]2[CH2:2][CH2:1]2)=[O:14])[CH:37]=[CH:36][C:35]=1[Cl:38])(=[O:41])=[O:40]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 15655Cyclopropanecarboxylic acidHCID 199401P,P-Diphenylphosphinic azideHCID 113680593-Amino-6-chloro-2-hydroxy-benzenesulfonamide

Product 1

HCID 9966285HCID 9966285, compoundYield 27.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Under Ar, the mixture of cyclopropanecarboxylic acid (500 mg, 5.81 mmol), diphenylphosphoryl azide (1.58 g, 5.81 mmol), and triethyl amine (0.81 mL, 5.8 mmol) in 3 mL of N,N-dimethyl-formamide was heated to 80° C. for 3 hours. The mixture was cooled to room temperature, 3-amino-6-chloro-2-hydroxybenzenesulfonamide (200 mg, 0.89 mmol) was added. The resulting mixture was stirred at room temperature for 20 hours. Purification upon Gilson HPLC, eluting with acetonitrile/water (10/90, v/v to 90/10, v/v, over 10 min), gave the desired product (74 mg, 27%). LC-MS (m/z) 306.2 (M+).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customPurification upon Gilson HPLC
  3. washeluting with acetonitrile/water (10/90, v/v to 90/10

Sources & evidence

ORD record
ord-5d60f0d4512c4d46acc325a4eeccf710
Source dataset
uspto-grants-2003_12
Patent number
US06664259B2

Reaction notes

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