Triethylamine → HCID 15614750, compound

HRID 620565Notes

Reaction equation

HRID 620565 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[NH:12][C:11](=[O:19])[CH:10]([CH2:20][NH2:21])[N:9]=1.[NH:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[C:23]1[C:31](Cl)=[O:32].C(N(CC)CC)C>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[NH:12][C:11](=[O:19])[CH:10]([CH2:20][NH:21][C:31]([C:23]2[NH:22][C:30]3[C:25]([CH:24]=2)=[CH:26][CH:27]=[CH:28][CH:29]=3)=[O:32])[N:9]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 118162081H-indole-2-carbonyl ChlorideHCID 15614835HCID 15614835, compound

Product 1

HCID 15614750HCID 15614750, compoundYield 32.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,3-Dihydro-5-(2-fluorophenyl)-3(RS)-aminomethyl-2H-1,4-benzodiazepin-2-one (80 mg, 0.282 mmole) and indole-2-carbonyl chloride (53 mg, 0.30 mmol) were mixed in 5 ml of methylene chloride at room temperature. The homogeneous reaction mixture was protected from moisture and treated with 42 l (0.30 mmole) of triethylamine. Within five min., triethylamine hydrochloride precipitated. The reaction mixture was stirred at room temperatre overnight and then partitioned between methylene chloride and saturated sodium bicarbonate solution. The resulting solid was collected, washed with water and dried over P2O5 at 70° C. In this way, 39 mg of the analytical product was obtained, m.p.: 315°-317° (d).

Workup

  1. customtriethylamine hydrochloride precipitated
  2. custompartitioned between methylene chloride and saturated sodium bicarbonate solution
  3. customThe resulting solid was collected
  4. washwashed with water
  5. dry with materialdried over P2O5 at 70° C

Sources & evidence

ORD record
ord-9d5bcd185aa041b781712501ffa45603
Source dataset
uspto-grants-1989_04
Patent number
US04820834

Reaction notes

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