1-Hydroxybenzotriazole → HCID 10210254, compound

HRID 1830100Notes

Reaction equation

HRID 1830100 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]([N:11]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[CH2:15][N:14]3[C:22]([C:25](O)=[O:26])=[CH:23][CH:24]=[C:13]3[CH2:12]2)=[O:10])[CH:6]=[CH:5][C:4]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[Cl:34].C(C1C=CC(OS(C(F)(F)F)(=O)=O)=C(OC)C=1)=O.ClC1C=CC=CC=1B(O)O.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[CH3:85][NH:86][CH2:87][C:88]1[CH:93]=[CH:92][CH:91]=[CH:90][N:89]=1>CN(C)C=O.O>[Cl:34][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[C:4]1[CH:5]=[CH:6][C:7]([C:9]([N:11]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[CH2:15][N:14]3[C:22]([C:25]([N:86]([CH3:85])[CH2:87][C:88]4[CH:93]=[CH:92][CH:91]=[CH:90][N:89]=4)=[O:26])=[CH:23][CH:24]=[C:13]3[CH2:12]2)=[O:10])=[CH:8][C:3]=1[O:2][CH3:1]

Participants

9

Reactant 6

HCID 757711-HydroxybenzotriazoleHCID 88757Methyl(2-pyridylmethyl)amineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27343222-Chlorophenylboronic acidHCID 108029624-Formyl-2-methoxyphenyl trifluoromethanesulfonateHCID 21947781HCID 21947781, compound

Product 1

HCID 10210254HCID 10210254, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 10-{[2-methoxy-2′-chloro[1,1′-biphenyl]-4-yl]carbonyl}-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxylic acid (0.230 g, 0.54 mmol) [prepared from trifluoromethanesulfonic acid 4-formyl-2-methoxy-phenyl ester of Example 7, Step A and 2-chlorophenyl boronic acid, in the manner of Example 7, Steps B–E], in N,N-dimethylformamide (15 mL) is added 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.120 g, 0.625 mmol) and 1-hydroxybenzotriazole (0.625 mmol). To the homogeneous solution was added methyl-pyridin-2-ylmethyl-amine (0.625 mmol) and the stirring was continued at room temperature overnight. At the end of this time the solution was poured into water and extracted with ethyl acetate. The combined extracts were washed with water, dried and concentrated and the residue was chromatographed on silica gel, eluting with 95:5 chloroform:methanol. The pure fractions were concentrated, and the residue azeotroped and triturated several times with hexane to yield the title product.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined extracts were washed with water
  3. customdried
  4. concentrationconcentrated
  5. customthe residue was chromatographed on silica gel
  6. washeluting with 95:5 chloroform
  7. concentrationThe pure fractions were concentrated
  8. customthe residue azeotroped
  9. customtriturated several times with hexane

Sources & evidence

ORD record
ord-f37d0bd2d4a842499304101f1570998e
Source dataset
uspto-grants-2006_06
Patent number
US07064120B2

Reaction notes

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