Dimethylformamide dimethyl acetal → HCID 59513563, compound

HRID 1159832Notes

Reaction equation

HRID 1159832 reaction equation
[CH3:1]OC(OC)N(C)C.FC(F)(F)C(O)=O.[CH3:16][N:17]([CH2:19][C:20]1[C:28]([OH:29])=[C:27]([F:30])[CH:26]=[C:25]2[C:21]=1[CH:22]=[CH:23][N:24]2[S:31]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)(=[O:33])=[O:32])[CH3:18]>CN(C=O)C>[F:30][C:27]1[CH:26]=[C:25]2[C:21]([CH:22]=[CH:23][N:24]2[S:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)(=[O:33])=[O:32])=[C:20]([CH2:19][N:17]([CH3:16])[CH3:18])[C:28]=1[O:29][CH3:1]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 68716432HCID 68716432, compound

Product 1

HCID 59513563HCID 59513563, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,N-dimethylformamide dimethyl acetal (0.964 ml, 7.233 mmol) was added to a solution of 4-[(dimethylamino)methyl]-6-fluoro-1-(phenylsulfonyl)-1H-indol-5-ol (252 mg, 0.723 mmol; Example 146) in DMF (8 ml) and the mixture was divided into two tubes and heated in microwave oven at 180 0 C for 180 s. Solvent was evaporated and residue purified on Gilson HPLC using 30-70% MeCN in 50 nM ammonium bicarbonate buffer as eluent (Xterra). Yield: 101.7 mg (39%); white solid. MS (ESI+) for C18H19FN2O3S m/z 363 (M+H)+.

Workup

  1. temperatureheated in microwave oven at 180 0 C for 180 s
  2. customSolvent was evaporated
  3. customresidue purified on Gilson HPLC

Sources & evidence

ORD record
ord-a476a3af35f54ba3bf958ce7ee6e1904
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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