Acetyl chloride → HCID 67343594, compound

HRID 1257667Notes

Reaction equation

HRID 1257667 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([N+:27]([O-:29])=[O:28])[C:18]([NH:19][C@H:20]4[CH2:25][CH2:24][CH2:23][C@H:22]([OH:26])[CH2:21]4)=[C:13]3[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)C(C)C)(C)C.[C:39](Cl)(=[O:41])[CH3:40]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([N+:27]([O-:29])=[O:28])[C:18]([NH:19][CH:20]4[CH2:25][CH2:24][CH2:23][CH:22]([O:26][C:39](=[O:41])[CH3:40])[CH2:21]4)=[C:13]3[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 131730632HCID 131730632, compound

Product 1

HCID 67343594HCID 67343594, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of Trans (racemic) 3-(1-Benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-cyclohexanol (8.84 g, 21.2 mmol) dissolved in DCM (5 ml) was added N,N-diisopropylethylamine (3.88 ml, 22.28 mmol), followed by 4-Dimethylamino pyridine (420.3 mg, 3.44 mmol) at room temperature. To this was added Acetyl chloride (6.04 ml, 84.90 mmol) dropwise with stirring at room temperature. The mixture was stirred for 4 hours at room temperature and concentrated under reduced pressure to give an oil, which was used, as is, for the next step. LCMS (Method M, ESI): RT=3.07 min, m+H=459.3.

Workup

  1. stirringThe mixture was stirred for 4 hours at room temperature
  2. concentrationconcentrated under reduced pressure
  3. customto give an oil, which

Sources & evidence

ORD record
ord-a14b69f1d1444575af94191c9388741a
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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