1-Hydroxybenzotriazole → HCID 10210196, compound

HRID 2053733Notes

Reaction equation

HRID 2053733 reaction equation
[Cl:1][C:2]1[C:3]([C:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH:30]=2)=[CH:4][C:5]([O:27][CH3:28])=[C:6]([CH:26]=1)[C:7]([N:9]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[CH2:13][N:12]2[C:20]([C:23]([OH:25])=O)=[CH:21][CH:22]=[C:11]2[CH2:10]1)=[O:8].[CH3:35][N:36]([CH3:42])[CH2:37][CH2:38][CH2:39][NH:40][CH3:41].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=N)C.C(N(CC)C(C)C)(C)C>C(OCC)(=O)C>[Cl:1][C:2]1[C:3]([C:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH:30]=2)=[CH:4][C:5]([O:27][CH3:28])=[C:6]([CH:26]=1)[C:7]([N:9]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[CH2:13][N:12]2[C:20]([C:23]([N:40]([CH2:39][CH2:38][CH2:37][N:36]([CH3:42])[CH3:35])[CH3:41])=[O:25])=[CH:21][CH:22]=[C:11]2[CH2:10]1)=[O:8]

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 783021,3-Propanediamine, N1,N1,N3-trimethyl-HCID 81531DiisopropylethylamineHCID 10299280HCID 10299280, compoundHCID 21883477Ethylcarbodiimide hydrochloride

Product 1

HCID 10210196HCID 10210196, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

10-(5-Chloro-4-cyclohex-1-en-1-yl-2-methoxybenzoyl)-10,11-dihydro-5H-pyrrolo [2,1-c][1,4]benzodiazepine-3-carboxylic acid of Example 1, Step G (0.200 g, 0.419 mmol), (3-dimethylaminopropyl)methylamine (0.074 mL, 0.503 mmol), 1-hydroxy benzotriazole (0.062 g, 0.461 mmol) and 1-[3-dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.088 g, 0.461 mmol) were combined in amine-free N,N-dimethylformamide (1.7 mL), followed by addition of N,N-diisopropylethyl amine (0.110 mL, 0.629 mmol). The reaction was stirred at room temperature for 12 hours, then diluted with ethyl acetate and washed with water, saturated aqueous sodium bicarbonate and brine. The combined aqueous washings were saturated with sodium chloride and extracted with ethyl acetate. The combined extracts were dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by flash column chromatography on silica gel eluting with 10% methanol in chloroform to provide the title compound (0.220 g) as a white powder, m.p. 116-119° C.

Workup

  1. washwashed with water, saturated aqueous sodium bicarbonate and brine
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined extracts were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography on silica gel eluting with 10% methanol in chloroform

Sources & evidence

ORD record
ord-8d2292aec3b54ffdad859e2c12db1432
Source dataset
uspto-grants-2008_02
Patent number
US07326700B2

Reaction notes

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