1-Hydroxybenzotriazole → HCID 22053644, compound

HRID 1830062Notes

Reaction equation

HRID 1830062 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:13]([Cl:14])=[CH:12][C:11]([C:15]([N:17]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[CH2:21][N:20]3[C:28]([C:31]([OH:33])=O)=[CH:29][CH:30]=[C:19]3[CH2:18]2)=[O:16])=[C:10]([O:34][CH3:35])[CH:9]=1.[CH3:36][NH:37][CH2:38][C:39]1[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=1.ON1C2C=CC=CC=2N=N1.[ClH:55].CN(C)CCCN=C=NCC.C(N(CC)C(C)C)(C)C>CN(C)C=O.C(Cl)(Cl)Cl>[Cl:55][C:4]1[CH:5]=[CH:6][CH:7]=[CH:2][C:3]=1[C:8]1[C:13]([Cl:14])=[CH:12][C:11]([C:15]([N:17]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[CH2:21][N:20]3[C:28]([C:31]([N:37]([CH3:36])[CH2:38][C:39]4[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=4)=[O:33])=[CH:29][CH:30]=[C:19]3[CH2:18]2)=[O:16])=[C:10]([O:34][CH3:35])[CH:9]=1

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 883933-(Methylaminomethyl)pyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10185723HCID 10185723, compound

Product 1

HCID 22053644HCID 22053644, compoundYield 75.1%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of the 10-[(2′,6-dichloro-3-methoxy-[1,1′-biphenyl]-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine carboxylic acid of Step C (0.250 g, 0.49 mmol) in N,N-dimethylformamide (2 mL) was added 3-(methylaminomethyl) pyridine (0,073 g, 0.59 mmol), 1-hydroxybenzotriazole (0.074 g, 0.54 mmol), 1-[3-(dimethylamino)propyl]-3-ethyl carbodiimide hydrochloride (0.093 g, 0.54 mmol), and N,N-diisopropylethyl amine (0.096 g, 0.74 mmol). After stirring overnight, the reaction mixture was taken up in chloroform, washed with saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate, filtered and evaporated to dryness. Trituration of the residue with ethyl acetate provided the title compound (0.225 g) as a white solid, m.p. 196–198° C., found to be 93.88% pure by analytical HPLC [Primesphere C-18 column (2.0×150 mm); mobile phase: 45/55 acetonitrile/water containing 0.1% phosphoric acid].

Workup

  1. washwashed with saturated aqueous sodium bicarbonate and brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-06b0eddc3fb44d16a29f1fcd4d0489a0
Source dataset
uspto-grants-2006_06
Patent number
US07064120B2

Reaction notes

Loading…