1-Hydroxybenzotriazole → HCID 69518974, compound

HRID 1180010Notes

Reaction equation

HRID 1180010 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.Cl.[F:35][C:36]([F:60])([F:59])[C:37]1[CH:38]=[CH:39][C:40]([O:43][C:44]2[CH:49]=[CH:48][C:47]([O:50][C:51]([N:53]3[CH2:58][CH2:57][NH:56][CH2:55][CH2:54]3)=[O:52])=[CH:46][CH:45]=2)=[N:41][CH:42]=1>CN(C=O)C.C(N(CC)CC)C.O>[F:60][C:36]([F:35])([F:59])[C:37]1[CH:38]=[CH:39][C:40]([O:43][C:44]2[CH:45]=[CH:46][C:47]([O:50][C:51]([N:53]3[CH2:54][CH2:55][N:56]([C:9](=[O:11])[CH2:8][C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][N:2]=4)[CH2:57][CH2:58]3)=[O:52])=[CH:48][CH:49]=2)=[N:41][CH:42]=1

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 853172-Pyridineacetic acid, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69518037HCID 69518037, compound

Product 1

HCID 69518974HCID 69518974, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8471TriethylamineSolvent2×

Procedure

Triethylamine (0.026 ml) was added to a stirred solution of (pyridin-2-yl)acetic acid hydrochloride (0.033 g, 0.19 mmol) in DMF (2.5 ml) at 0° C. 1-Hydroxy-benzotriazole containing 8% of water (0.034 g) and then 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.044 g) was added and the mixture was stirred for 50 min. Piperazine-1-carboxylic acid 4-(5-trifluoromethyl-pyridin-2-yloxy)-phenyl ester hydrochloride (0.070 g) in a mixture of DMF (1 ml) and triethylamine (0.032 ml) was added and stirring was continued over night at room temperature. The solvent was removed in vacuum and the residue was partitioned between dichloromethane (10 ml) and water (10 ml). The organic phase was washed with water (10 ml), dried over sodium sulfate, filtered and evaporated. The residue was triturated with ether-petroleumsether 1:1 and the (2+1 ml). The residue was dried to give the title compound. White solid, m.p. 143-146° C.; HPLC-MS m/z: IR (KBr) □ 1732 (C═O), 1643 (C═O).

Workup

  1. additionwas added
  2. stirringstirring
  3. waitwas continued over night at room temperature
  4. customThe solvent was removed in vacuum
  5. customthe residue was partitioned between dichloromethane (10 ml) and water (10 ml)
  6. washThe organic phase was washed with water (10 ml)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was triturated with ether-petroleumsether 1:1
  11. customThe residue was dried

Sources & evidence

ORD record
ord-8431afeb79af4994ba150c6119a316dc
Source dataset
uspto-grants-2007_10
Patent number
US07279470B2

Reaction notes

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