1,2-Dichloroethane → HCID 137194528, compound

HRID 1350524Notes

Reaction equation

HRID 1350524 reaction equation
[CH:1]([N:4]1[N:13]=[C:12]2[C:6]([C:7]([N:18]3[CH2:23][CH2:22][NH:21][C@@H:20]([CH2:24][CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH2:19]3)=[N:8][C:9]3[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=3[NH:11]2)=[N:5]1)([CH3:3])[CH3:2].C=O.[C:34](O[BH-](OC(=O)C)OC(=O)C)(=[O:36])C.[Na+].[C:48](=O)(O)[O-].[Na+].[Cl:53]CCCl>C(Cl)Cl.CO>[OH2:36].[ClH:53].[ClH:53].[CH:1]([N:4]1[N:13]=[C:12]2[C:6]([C:7]([N:18]3[CH2:23][CH2:22][N:21]([CH3:34])[C@@H:20]([CH2:24][CH2:25][C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH2:19]3)=[N:8][C:9]3[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=3[NH:11]2)=[N:5]1)([CH3:3])[CH3:2].[CH:1]([N:4]1[N:13]=[C:12]2[C:6]([C:7]([N:18]3[CH2:23][CH2:22][N:21]([CH3:48])[C@@H:20]([CH2:24][CH2:25][C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH2:19]3)=[N:8][C:9]3[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=3[NH:11]2)=[N:5]1)([CH3:3])[CH3:2].[ClH:53].[ClH:53]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 135797767HCID 135797767, compound

Product 1

HCID 137194528HCID 137194528, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Combine (S)-2-isopropyl-10-(3-phenethyl-piperazin-1-yl)-2,4-dihydro-1,2,3,4,9-pentaaza-benzo[f]azulene (0.59 g, 1.42 mmol)and 37% formaldehyde solution (0.13 mL, 1.56 mmol) in 1,2-dichloroethane (25 mL). Stir for 10 minutes and add sodium triacetoxy borohydride (0.451 g, 2.13 mmol). Stir an additional 30 minutes and then pour solution onto saturated sodium bicarbonate solution. Extract with methylene chloride to give the crude product. Silica gel chromatography, eluding with methylene chloride:methanol (100:2.5), gives the title compound as the free base. The dihydrochloride salt precipitates in ethyl acetate as a yellow solid: m.p. 200° C.; mass spectrum (ion spray): m/z=430 (M+1); Analysis for C25H33Cl2N7(0.5 H2O): calcd: C, 58.71; H, 6.70; N, 19.17; found: C, 58.77; H, 6.60; N, 19.05.

Workup

  1. stirringStir an additional 30 minutes
  2. extractionExtract with methylene chloride
  3. customto give the crude product

Sources & evidence

ORD record
ord-c88c1e8ce09b4c72adb3693886f2cd2f
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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