Dimethylacetamide → HCID 86700294, compound

HRID 879479Notes

Reaction equation

HRID 879479 reaction equation
[C:1]([O:5][C@@H:6]([C:12]1[C:28]([CH3:29])=[CH:27][C:15]2[N:16]=[C:17]([C:19]3[CH:24]=[C:23](Cl)[N:22]=[C:21]([Cl:26])[CH:20]=3)[S:18][C:14]=2[C:13]=1[C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2].[CH3:37][N:38]1[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1.CC(N(C)C)=O>C(O)C>[C:1]([O:5][C@@H:6]([C:12]1[C:28]([CH3:29])=[CH:27][C:15]2[N:16]=[C:17]([C:19]3[CH:24]=[C:23]([N:41]4[CH2:42][CH2:43][N:38]([CH3:37])[CH2:39][CH2:40]4)[N:22]=[C:21]([Cl:26])[CH:20]=3)[S:18][C:14]=2[C:13]=1[C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 31374DimethylacetamideHCID 531671-MethylpiperazineHCID 86700293HCID 86700293, compound

Product 1

HCID 86700294HCID 86700294, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A solution of (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2,6-dichloropyridin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate (10 mg), N-methylpiperazine (10 mg), and DMA (250 μL) were combined in a microwave tube and heated to 100° C. for 30 min. Reaction was cooled to 23° C. and diluted with absolute ethanol and was purified by reverse phase HPLC, eluting by 5-100% acetonitrile in H2O with 0.1% TFA to give the title compound. LCMS-ESI+: calc'd for C32H36Cl2N4O3S: 627.2, 629.2 (M+H+); Found: 627.2, 629.2 (M+H+).

Workup

  1. customReaction
  2. temperaturewas cooled to 23° C.
  3. customwas purified by reverse phase HPLC
  4. washeluting by 5-100% acetonitrile in H2O with 0.1% TFA

Sources & evidence

ORD record
ord-94c28cad646a4f029df7380f91c253fb
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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