Diisopropylethylamine → HCID 178451076, compound

HRID 1035700Notes

Reaction equation

HRID 1035700 reaction equation
[C:1]([O:5][C:6]([CH2:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]2[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][CH:16]=2)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].OC1C2N=NNC=2C=CC=1.Cl.C(N=C=NCCCN(C)C)C.C(N(C(C)C)CC)(C)C.[CH2:55]([C:62]1[S:66][C:65]([NH2:67])=[N:64][N:63]=1)[C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1>ClCCl.CN(C)C=O>[CH2:55]([C:62]1[S:66][C:65]([NH:67][C:19]([C:18]2[CH:17]=[CH:16][C:15]([C@H:12]3[CH2:13][CH2:14][C@H:9]([CH2:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:10][CH2:11]3)=[CH:23][CH:22]=2)=[O:21])=[N:64][N:63]=1)[C:56]1[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=1

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 7548235-Benzyl-1,3,4-thiadiazol-2-amineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178418300HCID 178418300, compoundHCID 178451081HCID 178451081, compound

Product 1

HCID 178451076HCID 178451076, compoundYield 67.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

3 g of trans-4-(4-tert-butoxycarbonylmethylcyclohexyl)benzoic acid (9.42 mmol, 1 eq.) are placed in 35 mL of a mixture of dichloromethane and dimethylformamide in a 250 mL round-bottomed flask under a nitrogen atmosphere, at room temperature. 1.528 g of hydroxybenzotriazole (11.1 mmol, 2 eq.), 2.168 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (11.1 mmol, 2 eq.), 3.11 mL of diisopropylethylamine (18.84 mmol, 2 eq.) and 2.162 g of 5-benzyl-1,3,4-thiadiazol-2-amine (11.1 mmol, 2 eq.) are successively added with stirring. The reaction mixture is stirred for 4 days at room temperature. The reaction medium is evaporated to dryness and diluted in water. The precipitate obtained is filtered off and washed with water. The solid obtained is dissolved in a minimum amount of dichloromethane and chromatographed on silica gel, eluting with a gradient of ethyl acetate in dichloromethane ranging from 2.5% to 25%. 3.13 g of tert-butyl trans-{4-[4-(5-benzyl[1.3.4]thiadiazol-2-ylcarbamoyl)phenyl)cyclohexyl}acetate are obtained.

Workup

  1. stirringThe reaction mixture is stirred for 4 days at room temperature
  2. customThe reaction medium is evaporated to dryness
  3. additiondiluted in water
  4. customThe precipitate obtained
  5. filtrationis filtered off
  6. washwashed with water
  7. customThe solid obtained
  8. customchromatographed on silica gel
  9. washeluting with a gradient of ethyl acetate in dichloromethane ranging from 2.5% to 25%

Sources & evidence

ORD record
ord-a9cad11f839d4e73972fa807d2b28ffd
Source dataset
uspto-grants-2013_10
Patent number
US08546391B2

Reaction notes

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