Diisopropylethylamine → HCID 178425729, compound

HRID 1255501Notes

Reaction equation

HRID 1255501 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]2[N:6]3[C:10]([CH2:11][NH:12][CH2:13][C:4]=2[CH:3]=1)=[N:9][N:8]=[C:7]3[C@H:14]1[CH2:19][CH2:18][C@H:17]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[N:22]=2)[CH2:16][CH2:15]1.C(N(CC)C(C)C)(C)C.[F:39][CH:40]([F:50])[CH2:41]OS(C(F)(F)F)(=O)=O>ClCCl>[Cl:1][C:2]1[CH:29]=[CH:28][C:5]2[N:6]3[C:10]([CH2:11][N:12]([CH2:41][CH:40]([F:50])[F:39])[CH2:13][C:4]=2[CH:3]=1)=[N:9][N:8]=[C:7]3[C@H:14]1[CH2:19][CH2:18][C@H:17]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[N:22]=2)[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27740892,2-Difluoroethyl trifluoromethanesulfonateHCID 178425728HCID 178425728, compound

Product 1

HCID 178425729HCID 178425729, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of trans-8-chloro-1-[4-(6-methyl-pyridin-2-yloxy)-cyclohexyl]-5,6-dihydro-4H-2,3,5,10b-tetraaza-benzo[e]azulene (0.10 g, 0.24 mmol) and N,N-diisopropylethylamine (0.080 ml, 0.49 mmol) in dichloromethan (1 ml) was treated with trifluoro-methanesulfonic acid 2,2-difluoro-ethyl ester (63 mg, 0.29 mmol) at 0° C. The cooling bath was removed after 30 min. and the reaction mixture was stirred at room temperature over night. The mixture was partitioned between aqueous saturated ammonium chloride solution (50 ml) and ethyl acetate (50 ml). The aqueous layer was extracted with one 50-ml portion of ethyl acetate. The combined organic layers were washed with two 50-ml portions of a 1 M aqueous solution of sodium carbonate. The aqueous layers were each extracted with one 50-ml portion of ethyl acetate. The organic layers were dried over anhydrous sodium sulfate and concenrated in vacuo. Purification by flash column chromatography gave the title compound (98 mg, 85%) as white solid.

Workup

  1. customThe cooling bath was removed after 30 min.
  2. customThe mixture was partitioned between aqueous saturated ammonium chloride solution (50 ml) and ethyl acetate (50 ml)
  3. extractionThe aqueous layer was extracted with one 50-ml portion of ethyl acetate
  4. washThe combined organic layers were washed with two 50-ml portions of a 1 M aqueous solution of sodium carbonate
  5. extractioneach extracted with one 50-ml portion of ethyl acetate
  6. dry with materialThe organic layers were dried over anhydrous sodium sulfate
  7. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-70a445ad950d4810aeca43808764b57c
Source dataset
uspto-grants-2013_06
Patent number
US08461152B2

Reaction notes

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