Triethylamine → HCID 10207464, compound

HRID 396295Notes

Reaction equation

HRID 396295 reaction equation
[CH2:1]([O:8][C:9]1[C:17]2[C:12](=[N:13][CH:14]=[CH:15][CH:16]=2)[S:11][C:10]=1C(O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:28])C=CC=CC=1.[NH2:38][C:39]1[C:40]([OH:50])=[C:41]([S:46]([NH2:49])(=[O:48])=[O:47])[C:42]([Cl:45])=[CH:43][CH:44]=1.C([N:53]([CH2:56]C)CC)C>CN(C)C=O>[NH2:49][S:46]([C:41]1[C:40]([OH:50])=[C:39]([NH:38][C:56]([NH:53][C:10]2[S:11][C:12]3=[N:13][CH:14]=[CH:15][CH:16]=[C:17]3[C:9]=2[O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:28])[CH:44]=[CH:43][C:42]=1[Cl:45])(=[O:48])=[O:47]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 1478615HCID 1478615, compoundHCID 113680593-Amino-6-chloro-2-hydroxy-benzenesulfonamide

Product 1

HCID 10207464HCID 10207464, compoundYield 26.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Under Ar, the mixture of 3-(benzyloxy)thieno[2,3-b]pyridine-2-carboxylic acid (150 mg, 0.53 mmol) in 2 mL of N,N-dimethyl-formamide was heated to 80° C. Diphenylphosphoryl azide (146 mg, 0.53 mmol), 3-amino-6-chloro-2-hydroxybenzenesulfonamide (117 mg, 0.53 mmol) and triethyl amine (0.054 mL, 0.53 mmol) were added. The resulting mixture was heated for another 18 hours. when kept temperature at 70° C. Purification upon Gilson HPLC, eluting with acetonitrile/water (10/90, v/v to 90/10, v/v, over 10 min), gave the desired product (70 mg, 26%). LC-MS (m/z) 505.2 (M+).

Workup

  1. temperatureThe resulting mixture was heated for another 18 hours
  2. customat 70° C
  3. customPurification upon Gilson HPLC
  4. washeluting with acetonitrile/water (10/90, v/v to 90/10

Sources & evidence

ORD record
ord-5e7437694c1e49e6845a7260c55564cb
Source dataset
uspto-grants-2003_08
Patent number
US06608077B2

Reaction notes

Loading…