Acetic Acid → HCID 178456168, compound

HRID 452542Notes

Reaction equation

HRID 452542 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]2[N:6]3[C:10]([CH2:11][NH:12][CH2:13][C:4]=2[CH:3]=1)=[N:9][N:8]=[C:7]3[C@H:14]1[CH2:19][CH2:18][C@H:17]([C:20]2[C:25]([F:26])=[CH:24][CH:23]=[CH:22][N:21]=2)[CH2:16][CH2:15]1.[CH3:29][C:30]([CH3:32])=O.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(N(C(C)C)C(C)C)C>ClCCCl.CO>[Cl:1][C:2]1[CH:28]=[CH:27][C:5]2[N:6]3[C:10]([CH2:11][N:12]([CH:30]([CH3:32])[CH3:29])[CH2:13][C:4]=2[CH:3]=1)=[N:9][N:8]=[C:7]3[C@H:14]1[CH2:19][CH2:18][C@H:17]([C:20]2[C:25]([F:26])=[CH:24][CH:23]=[CH:22][N:21]=2)[CH2:16][CH2:15]1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 180AcetoneHCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 178505857HCID 178505857, compound

Product 1

HCID 178456168HCID 178456168, compoundYield 72.2%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 887MethanolSolvent

Procedure

After stirring a solution of trans-8-chloro-1-[4-(3-fluoro-pyridin-2-yl)-cyclohexyl]-5,6-dihydro-4H-2,3,5,10b-tetraaza-benzo[e]azulene (50.0 mg, 0.126 mmol), acetone (0.019 ml, 0.251 mmol) and acetic acid (0.014 ml, 0.25 mmol) in 1,2-dichloroethane (1.3 ml) at room temperature for 5 h, sodium triacetoxyborohydride (58.6 mg, 0.276 mmol) was added. Stirring for further 20 h was followed by quenching with methanol (1 ml) and N-ethyldiisopropylamine (0.044 ml, 0.25 mmol). The reaction mixture was stirred for 30 minutes and concentrated in vacuo. Preparative RP-HPLC with water (0.05% formic acid)/methanol as eluent gave the title compound (40 mg, 72%) as white solid. MS m/e: 440 ([M+H]+)

Workup

  1. stirringThe reaction mixture was stirred for 30 minutes
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0adce473fc614829bb0d47b7c0ab7f8c
Source dataset
uspto-grants-2013_07
Patent number
US08492376B2

Reaction notes

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