1,2-Dichloroethane → HCID 86690951, compound

HRID 714746Notes

Reaction equation

HRID 714746 reaction equation
ClC1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][C@H:14]([OH:19])[C:15]([F:18])([F:17])[F:16])[C:11](=[O:20])[N:10]([CH2:21][C:22]3[CH:27]=[C:26]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[C:34]([F:37])([F:36])[F:35])[C:25]([C:38]([OH:40])=O)=[CH:24][CH:23]=3)[N:9]=2)=[CH:4]C=1.C1C=CC2N(O)N=[N:47]C=2C=1.[CH2:51]([Cl:54])[CH2:52]Cl.N>CN(C=O)C.O>[Cl:54][C:51]1[CH:52]=[CH:4][C:5]([C:8]2[N:12]([CH2:13][C@H:14]([OH:19])[C:15]([F:17])([F:16])[F:18])[C:11](=[O:20])[N:10]([CH2:21][C:22]3[CH:27]=[C:26]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[C:34]([F:35])([F:36])[F:37])[C:25]([C:38]([NH2:47])=[O:40])=[CH:24][CH:23]=3)[N:9]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 222Ammonia2×HCID 757711-HydroxybenzotriazoleHCID 86690950HCID 86690950, compound

Product 1

HCID 86690951HCID 86690951, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

208 mg (0.36 mmol) of the compound from Example 141 were initially charged in 5 ml of DMF, and 62 mg (0.46 mmol) of HOBt and 88 mg (0.46 mmol) of EDC were added. After 10 min of stirring at RT, 1.0 ml (16 mmol) of ammonia solution (33% strength in water) were added, and the mixture was stirred at RT for 16 h. Under reduced pressure, the reaction solution was then freed from excess ammonia, about 3 ml of water were added and the mixture was extracted three times with in each case 5 ml of ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified chromatographically [Method 19]. This gave 85 mg (39% of theory) of the target compound.

Workup

  1. stirringthe mixture was stirred at RT for 16 h
  2. additionwere added
  3. extractionthe mixture was extracted three times with in each case 5 ml of ethyl acetate
  4. dry with materialThe combined organic phases were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified chromatographically [Method 19]

Sources & evidence

ORD record
ord-89ad313c2157456a9666cbbf198f6786
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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