Triethylamine → (4-(9H-benzo[f]pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]diazepin-3-yl)phenyl)methanol

HRID 44229Notes

Reaction equation

HRID 44229 reaction equation
Cl[C:2]1[C:3]2[CH:16]=[CH:15][CH:14]=[CH:13][C:4]=2[NH:5][C:6]2[N:12]=[CH:11][CH:10]=[CH:9][C:7]=2[N:8]=1.[OH:17][CH2:18][C:19]1[CH:28]=[CH:27][C:22]([C:23]([NH:25][NH2:26])=O)=[CH:21][CH:20]=1.C(N(CC)CC)C>CC(N(C)C)=O>[N:26]1[N:25]=[C:23]([C:22]2[CH:27]=[CH:28][C:19]([CH2:18][OH:17])=[CH:20][CH:21]=2)[N:8]2[C:2]=1[C:3]1[CH:16]=[CH:15][CH:14]=[CH:13][C:4]=1[NH:5][C:6]1[N:12]=[CH:11][CH:10]=[CH:9][C:7]2=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 432368204-(Hydroxymethyl)benzohydrazideHCID 1361637716-chloro-11H-benzo[e]pyrido[3,2-b][1,4]diazepine

Product 1

HCID 136163785(4-(9H-benzo[f]pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]diazepin-3-yl)phenyl)methanol

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of 6-chloro-11H-benzo[e]pyrido[3,2-b][1,4]diazepine (4.3 g, 19 mmol), 4-(hydroxymethyl)benzohydrazide (3.2 g, 20 mmol) and triethylamine (2.8 mL, 20 mmol) in dimethylacetamide (100 mL) was stirred at 85° C. until the starting material is all consumed (as followed by LC/MS). The reaction mixture was diluted with dichloromethane (100 mL) and water (100 mL). The phases were separated and the aqueous phase was extracted with dichloromethane (3×100 mL). The combined organic extracts were washed with water (3×100 mL), dried over sodium sulfate and concentrated in vacuo. The residue was triturated with ethyl acetate (20 mL) and the solid was collected by filtration. The (4-(9H-benzo[f]pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]diazepin-3-yl)phenyl)methanol was obtained as a yellow solid (4.8 g, 74%). M.p.=276-278° C.; 400 MHz 1H NMR (DMSO-d6) δ: 8.78 (s, 1H), 8.21 (dd, J=4.8, 1.6 Hz, 1H), 7.96 (dd, J=7.2, 1.6 Hz, 1H), 7.50-7.33 (m, 6H), 7.17-7.12 (m, 2H), 6.91 (dd, J=8.0, 4.8 Hz, 1H), 5.33 (t, J=5.6 Hz, 1H), 4.55 (d, J=6.0 Hz, 2H); LCMS [M+H]: 342.

Workup

  1. customall consumed (as followed by LC/MS)
  2. additionThe reaction mixture was diluted with dichloromethane (100 mL) and water (100 mL)
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted with dichloromethane (3×100 mL)
  5. washThe combined organic extracts were washed with water (3×100 mL)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was triturated with ethyl acetate (20 mL)
  9. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-1c65ff2f834342fb81bcefebd77b3f24
Source dataset
uspto-grants-2013_09
Patent number
US08541407B2

Reaction notes

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