Acetic Acid → 4-(2-Diisopropylamino-ethylamino)benzenesulfonic acid 2-acetylaminobenzothiazol-6-yl ester

HRID 1867980Notes

Reaction equation

HRID 1867980 reaction equation
[C:1](O)(=[O:3])[CH3:2].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:38][C:39]1[S:40][C:41]2[CH:47]=[C:46]([O:48][S:49]([C:52]3[CH:57]=[CH:56][C:55]([NH:58][CH2:59][CH2:60][N:61]([CH:65]([CH3:67])[CH3:66])[CH:62]([CH3:64])[CH3:63])=[CH:54][CH:53]=3)(=[O:51])=[O:50])[CH:45]=[CH:44][C:42]=2[N:43]=1>CN(C)C=O.O>[C:1]([NH:38][C:39]1[S:40][C:41]2[CH:47]=[C:46]([O:48][S:49]([C:52]3[CH:57]=[CH:56][C:55]([NH:58][CH2:59][CH2:60][N:61]([CH:65]([CH3:67])[CH3:66])[CH:62]([CH3:63])[CH3:64])=[CH:54][CH:53]=3)(=[O:51])=[O:50])[CH:45]=[CH:44][C:42]=2[N:43]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 579808584-(2-Diisopropylaminoethylamino)benzenesulfonic acid 2-aminobenzothiazol-6-yl ester2×

Product 1

HCID 579808364-(2-Diisopropylamino-ethylamino)benzenesulfonic acid 2-acetylaminobenzothiazol-6-yl esterYield 19.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

28 mg of acetic acid, 177.5 mg of HBTU and 163 μl of DIEA are added to a solution of 4-(2-diisopropylaminoethylamino)benzenesulfonic acid 2-amino-benzothiazol-6-yl ester (intermediate 34) (70 mg, 0.156 mmol) in 4 ml of dimethylformamide. The solution obtained is stirred for 20 hours at room temperature. After addition of 50 ml of water, the reaction mixture is extracted with 3 times 25 ml of ethyl acetate. The extracts are dried over magnesium sulfate, filtered and evaporated under reduced pressure to give 130 mg of crude oil. This oil is purified by LC/MS to give 15 mg of 4-(2-diisopropylamino-ethylamino)benzenesulfonic acid 2-acetylaminobenzothiazol-6-yl ester.

Workup

  1. customThe solution obtained
  2. extractionthe reaction mixture is extracted with 3 times 25 ml of ethyl acetate
  3. dry with materialThe extracts are dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customto give 130 mg of crude oil
  7. customThis oil is purified by LC/MS

Sources & evidence

ORD record
ord-3a47aeec3ec3416690f894099b8fdba0
Source dataset
uspto-grants-2009_12
Patent number
US07632952B2

Reaction notes

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