Diisopropylethylamine → HCID 178451366, compound

HRID 1035724Notes

Reaction equation

HRID 1035724 reaction equation
[C:1]([O:5][C:6]([CH2:8][O:9][C@H:10]1[CH2:15][CH2:14][C@H:13]([C:16]2[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[CH:18][CH:17]=2)[CH2:12][CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.OC1C2N=NNC=2C=CC=1.Cl.C(N=C=NCCCN(C)C)C.[CH2:56]([C:63]1[S:67][C:66]([NH2:68])=[N:65][N:64]=1)[C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1>ClCCl>[CH2:56]([C:63]1[S:67][C:66]([NH:68][C:20]([C:19]2[CH:23]=[CH:24][C:16]([C@H:13]3[CH2:12][CH2:11][C@H:10]([O:9][CH2:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:15][CH2:14]3)=[CH:17][CH:18]=2)=[O:21])=[N:65][N:64]=1)[C:57]1[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 7548235-Benzyl-1,3,4-thiadiazol-2-amineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2×HCID 178418300HCID 178418300, compound2×HCID 178451367HCID 178451367, compound

Product 1

HCID 178451366HCID 178451366, compoundYield 9.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.6 g of trans-4-(4-tert-butoxycarbonylmethoxycyclohexyl)benzoic acid (1.79 mmol, 1 eq.) is placed in 8 mL of dichloromethane with stirring. 0.7 mL of diisopropylethylamine (4.49 mmol, 2.5 eq.), 0.275 g of hydroxybenzotriazole (1.79 mmol, 1 eq.) and 0.413 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.15 mmol, 1.2 eq.) are successively added, followed, after 10 minutes, by addition of 0.377 g of 5-benzyl-1,3,4-thiadiazol-2-amine (1.97 mmol, 1.1 eq.). After 16 hours, 0.137 g of hydroxybenzotriazole (0.895 mmol, 0.5 eq.) and 0.172 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.17 mmol, 0.5 eq.) are added. After 18 hours, the medium is evaporated, diluted with ethyl acetate and washed three times with brine. The organic phase is dried over sodium sulfate, filtered and evaporated. The residue is chromatographed on silica gel with a gradient of methanol in dichloromethane ranging from 0% to 2%. 0.09 g of tert-butyl trans-{4-[4-(5-benzyl[1.3.4]thiadiazol-2-ylcarbamoyl)phenyl]cyclohexyloxy}acetate is obtained.

Workup

  1. waitAfter 18 hours
  2. customthe medium is evaporated
  3. additiondiluted with ethyl acetate
  4. washwashed three times with brine
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is chromatographed on silica gel with a gradient of methanol in dichloromethane ranging from 0% to 2%

Sources & evidence

ORD record
ord-8fc89ded6df14456b09ab3555e5bd3de
Source dataset
uspto-grants-2013_10
Patent number
US08546391B2

Reaction notes

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