Triethylamine → HCID 16039366, compound

HRID 639284Notes

Reaction equation

HRID 639284 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([O:6][CH2:7][C:8]([N:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[CH2:14][N:13]3[C:21]([C:24](Cl)=[O:25])=[CH:22][CH:23]=[C:12]3[CH2:11]2)=[O:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl.[CH3:37][C:38]1[C:43]([NH2:44])=[CH:42][CH:41]=[C:40]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=2[CH3:51])[CH:39]=1>O1CCCC1>[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([O:6][CH2:7][C:8]([N:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[CH2:14][N:13]3[C:21]([C:24]([NH:44][C:43]4[CH:42]=[CH:41][C:40]([C:45]5[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=5[CH3:51])=[CH:39][C:38]=4[CH3:37])=[O:25])=[CH:22][CH:23]=[C:12]3[CH2:11]2)=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1488202',3-Dimethyl-4-aminobiphenyl hydrochlorideHCID 86607493HCID 86607493, compound

Product 1

HCID 16039366HCID 16039366, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 10-[2-(4-chloro-phenoxy)-acetyl]-10,11-dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepine-3-carbonyl chloride of step B (0.415 mmol) in anhydrous tetrahydrofuran (3 mL) was added triethylamine (0.829 mmol) and 3,2′-dimethylbiphen-4-ylamine hydrochloride (0.415 mmol). The solution was stirred for 18 hours at ambient temperature. The solvent was evaporated, the residue was taken up in dichloromethane, washed with water, dried over anhydrous sodium sulfate, and evaporated. Chromatography on silica gel using 55:23:22 hexane/ethyl acetate/dichloromethane as eluant gave the title compound as an amorphous solid. This was crystallized from ethyl acetate/hexane to afford 0.17 g of the title product (71% yield), m.p. 159-161° C. MS [(+)ESI, m/z]: 576 [M+H]+ Anal. Calcd for C35H30CIN3O3: C, 72.97; H, 5.25; N, 7.29. Found: C, 72.59; H, 5.28; N, 7.24.

Workup

  1. customThe solvent was evaporated
  2. washwashed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-a2536bb5ca904b5db659b6dc7f971f0f
Source dataset
uspto-grants-2010_04
Patent number
US07691848B2

Reaction notes

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