Triethylamine → HCID 9836721, compound

HRID 432612Notes

Reaction equation

HRID 432612 reaction equation
[CH:1]1(C(O)=O)[CH2:4][CH2:3][CH2:2]1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:15])C=CC=CC=1.C([N:27]([CH2:30]C)CC)C.[NH2:32][C:33]1[C:34]([OH:44])=[C:35]([S:40]([NH2:43])(=[O:42])=[O:41])[C:36]([Cl:39])=[CH:37][CH:38]=1>CN(C)C=O>[NH2:43][S:40]([C:35]1[C:34]([OH:44])=[C:33]([NH:32][C:30]([NH:27][CH:1]2[CH2:2][CH2:3][CH2:4]2)=[O:15])[CH:38]=[CH:37][C:36]=1[Cl:39])(=[O:42])=[O:41]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 19494Cyclobutanecarboxylic acidHCID 199401P,P-Diphenylphosphinic azideHCID 113680593-Amino-6-chloro-2-hydroxy-benzenesulfonamide

Product 1

HCID 9836721HCID 9836721, compoundYield 17.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Under Ar, the mixture of cyclobutanecarboxylic acid (250 mg, 2.50 mmol), diphenylphosphoryl azide (756 mg, 2.74 mmol), and triethyl amine (0.38 mL, 2.74 mmol) in 3 mL of N,N-dimethyl-formamide was heated to 80° C. for 2 hours. The mixture was cooled to room temperature, 3-amino-6-chloro-2hydroxybenzenesulfonamide (556 mg, 2.50 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 (137 mg, 17%). LC-MS (m/z) 320.0 (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-c98fbd52602344d6acb5ca0c2ea4fe60
Source dataset
uspto-grants-2003_12
Patent number
US06664259B2

Reaction notes

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