Triethylamine → HCID 178467358, compound

HRID 1895510Notes

Reaction equation

HRID 1895510 reaction equation
Cl.[Cl:2][CH2:3][CH:4]([NH2:9])[CH2:5][CH:6]([CH3:8])[CH3:7].C(N(CC)CC)C.[CH2:17]([O:19][C:20]1[N:21]([CH2:32][C:33]2[CH:38]=[CH:37][C:36]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=3[C:45]3[NH:49][N:48]=[N:47][N:46]=3)=[CH:35][CH:34]=2)[C:22]2[C:28]([C:29](O)=[O:30])=[CH:27][CH:26]=[CH:25][C:23]=2[N:24]=1)[CH3:18].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[Cl:2][CH2:3][CH:4]([NH:9][C:29]([C:28]1[C:22]2[N:21]([CH2:32][C:33]3[CH:38]=[CH:37][C:36]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=4[C:45]4[NH:49][N:48]=[N:47][N:46]=4)=[CH:35][CH:34]=3)[C:20]([O:19][CH2:17][CH3:18])=[N:24][C:23]=2[CH:25]=[CH:26][CH:27]=1)=[O:30])[CH2:5][CH:6]([CH3:8])[CH3:7]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86631166HCID 86631166, compoundHCID 178467362HCID 178467362, compound

Product 1

HCID 178467358HCID 178467358, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-Chloromethyl-3-methylbutylamine hydrochloride (39 mg, 230 μmol) and triethylamine (31.6 μL, 1 equiv) were dissolved in DCM (2.00 mL). 2-Ethoxy-3-[2′-(1H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-3H-benzimidazole-4-carboxylic acid (100 mg, 1 equiv) was added, followed by HOBt (31 mg, 1 equiv) and EDC HCl (51 mg, 1.1 equiv). The reaction was stirred overnight at room temperature, then diluted with DCM (10 mL), washed (H2O, 10 mL), dried over NaSO4, decanted, and the solvent evaporated. The residue was purified by flash chromatography (5% MeOH/DCM) to afford the title compound as a white solid (19 mg, 15%). ESMS [M+H]+ calcd for C30H32ClN7O2 557.3. found 558.3.

Workup

  1. washwashed (H2O, 10 mL)
  2. dry with materialdried over NaSO4
  3. customdecanted
  4. customthe solvent evaporated
  5. customThe residue was purified by flash chromatography (5% MeOH/DCM)

Sources & evidence

ORD record
ord-2fa991a7c45c4c43a11425ff7b4237e8
Source dataset
uspto-grants-2013_08
Patent number
US08513432B2

Reaction notes

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