Dicyclohexylcarbodiimide → HCID 75989777, compound

HRID 2402605Notes

Reaction equation

HRID 2402605 reaction equation
[CH3:1][N:2]1[C:6]([C:7](=[N:14][O:15][CH2:16][C:17]2[N:18]=[C:19]([NH2:22])[S:20][CH:21]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:5][N:4]=[N:3]1.[O:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:26][CH2:25][CH:24]1[C:33](O)=[O:34].N1(O)C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[CH3:1][N:2]1[C:6]([C:7](=[N:14][O:15][CH2:16][C:17]2[N:18]=[C:19]([NH:22][C:33]([CH:24]3[CH2:25][CH2:26][C:27]4[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=4)[O:23]3)=[O:34])[S:20][CH:21]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:5][N:4]=[N:3]1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 27236653,4-dihydro-2H-1-benzopyran-2-carboxylic acidHCID 866531284-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]-1,3-thiazol-2-amine

Product 1

HCID 75989777HCID 75989777, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]-1,3-thiazol-2-amine (200 mg, 0.63 mmol) in dimethylformamide (1.5 mL) were added chromane-2-carboxylic acid (124 mg, 0.70 mmol) and 1H-benzotriazol-1-ol (94 mg, 0.70 mmol). The reaction mixture was poured at room temperature on a cartridge filled with 1.44 g of silica linked with N,N′-dicyclohexylcarbodiimide (loading: 1.05 mmol/g). After one night at room temperature, the cartridge was eluted with 1 mL of dimethylformamide. The filtrated solution was then poured on a cartridge filled with 1.5 g of basic alumina. After 2 hours of reaction a room temperature, the cartridge was rinsed twice with 10 mL of ethyl acetate. The combined filtrated solutions were evaporated in vacuo to yield a yellow oil. Purification on silica gel afforded of N-{4-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]-1,3-thiazol-2-yl}chromane-2-carboxamide as a colorless oil [150 mg, yield 44%; HPLC/MS: nm/z=476 (M+H); log P(HCOOH)=3.78].

Workup

  1. additionThe reaction mixture was poured at room temperature on a cartridge
  2. additionfilled with 1.44 g of silica
  3. waitAfter one night at room temperature
  4. washthe cartridge was eluted with 1 mL of dimethylformamide
  5. additionThe filtrated solution was then poured on a cartridge
  6. additionfilled with 1.5 g of basic alumina
  7. customAfter 2 hours of reaction a room temperature
  8. washthe cartridge was rinsed twice with 10 mL of ethyl acetate
  9. filtrationThe combined filtrated solutions
  10. customwere evaporated in vacuo
  11. customto yield a yellow oil
  12. customPurification on silica gel

Sources & evidence

ORD record
ord-935243e5e4b94877b2118a29f2add524
Source dataset
uspto-grants-2014_08
Patent number
US08796463B2

Reaction notes

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