Benzoyl chloride → HCID 22180074, compound

HRID 1795993Notes

Reaction equation

HRID 1795993 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2=[CH:15][CH:16]=[CH:17][N:11]2[N:10]=[C:9]1[CH:18]([NH:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:19][CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:29](Cl)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.CCN(CC)CC>C(Cl)(Cl)Cl>[CH2:22]([N:21]([CH:18]([C:9]1[N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:13](=[O:14])[C:12]2=[CH:15][CH:16]=[CH:17][N:11]2[N:10]=1)[CH2:19][CH3:20])[C:29](=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 22180079HCID 22180079, compound

Product 1

HCID 22180074HCID 22180074, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
25 °C

Procedure

3-Benzyl-2-(1-benzylamino-propyl)-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one (Example 42, 23.1 mg, 0.062 mmol) in CHCl3 (5 mL) was treated with benzoylchloride (28.8 μL, 0.248 mmol) and Et3N (23.0 μL, 0.166 mmol), then stirred for 18 h at 25° C. The mixture was concentrated under vacuum and purified by preparative HPLC using a YMC S10 ODS 20×100 mm column affording the desired compound (22 mg, 83%) as a colorless film: LC/MS 87% at 3.72 min (ESI+) 477 (M++H).

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-54f6ecc4b3ad4ddfb38078763c1c4d6e
Source dataset
uspto-grants-2006_04
Patent number
US07030118B2

Reaction notes

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