1-Hydroxybenzotriazole → HCID 86755696, compound

HRID 1872768Notes

Reaction equation

HRID 1872768 reaction equation
[CH3:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[C:11]([OH:13])=O.ON1C2C=CC=CC=2N=N1.[CH3:24][C:25]1[O:26][C:27]([CH2:30][N:31]2[C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=3[N:33]=[C:32]2[NH:40][CH:41]2[CH2:46][CH2:45][N:44]([C@@H:47]3[CH2:52][CH2:51][NH:50][C@@H:49]([CH2:53][C:54]4[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=4)[CH2:48]3)[CH2:43][CH2:42]2)=[CH:28][N:29]=1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.C(N(CC)CC)C>[CH3:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[C:11]([N:50]1[CH2:51][CH2:52][C@@H:47]([N:44]2[CH2:43][CH2:42][CH:41]([NH:40][C:32]3[N:31]([CH2:30][C:27]4[O:26][C:25]([CH3:24])=[N:29][CH:28]=4)[C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=4[N:33]=3)[CH2:46][CH2:45]2)[CH2:48][C@@H:49]1[CH2:53][C:54]1[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=1)=[O:13]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 6005913-Methyl-1-benzofuran-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86755697HCID 86755697, compound

Product 1

HCID 86755696HCID 86755696, compoundYield 45.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

3-methyl-2-benzofurancarboxylic acid (0.100 g) and 1-hydroxy-1H-benzotriazole (0.070 g) were added to (±)-trans-1-[(2-methyl-5-oxazolyl)methyl]-N-[1-[2-(phenylmethyl)-4-piperidinyl]-4-piperidinyl]-1H-benzimidazol-2-amine (0.100 g) in CH2Cl2 (5 ml). The mixture was stirred under N2 atmosphere. A solution of triethylamine (0.5 ml) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1:1) (0.080 g) in CH2Cl2 (10 ml) was added dropwise and the reaction mixture was stirred overnight at RT, under N2. Then, the compound was isolated and purified by column chromatography (eluent gradient: (0.5% ammoniumacetate in H2O)/CH3OH/CH3CN 70/15/15 upgrading over 0/50/50 to 0/0/100). The desired fractions were collected and the solvent was evaporated, yielding 0.060 g of (±)-trans-1-[(3-methyl-2-benzofuranyl)-carbonyl]-4-[4-[[1-[(2-methyl-5-oxazolyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]-2-(phenylmethyl)piperidine.

Workup

  1. stirringthe reaction mixture was stirred overnight at RT, under N2
  2. customThen, the compound was isolated
  3. custompurified by column chromatography (eluent gradient: (0.5% ammoniumacetate in H2O)/CH3OH/CH3CN 70/15/15 upgrading over 0/50/50 to 0/0/100)
  4. customThe desired fractions were collected
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-940d9e79793a41cd8b8e395babffb459
Source dataset
uspto-grants-2000_08
Patent number
US06110939

Reaction notes

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