Acetic Acid → HCID 178477850, compound

HRID 446755Notes

Reaction equation

HRID 446755 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([C@H:10]2[CH2:15][CH2:14][C@H:13]([C:16]3[N:25]4[C:19]([CH2:20][NH:21][CH2:22][C:23]5[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:24]=54)=[N:18][N:17]=3)[CH2:12][CH2:11]2)=[N:2]1.[C:31]1(=O)[CH2:34][CH2:33][CH2:32]1.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>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([C@H:10]2[CH2:15][CH2:14][C@H:13]([C:16]3[N:25]4[C:19]([CH2:20][N:21]([CH:31]5[CH2:34][CH2:33][CH2:32]5)[CH2:22][C:23]5[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:24]=54)=[N:18][N:17]=3)[CH2:12][CH2:11]2)=[N:2]1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 14496CyclobutanoneHCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 178477855HCID 178477855, compound

Product 1

HCID 178477850HCID 178477850, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 887MethanolSolvent

Procedure

A solution of trans-1-(4-benzo[d]isothiazol-3-yl-cyclohexyl)-8-chloro-5,6-dihydro-4H-2,3,5,10b-tetraaza-benzo[e]azulene (35.0 mg, 0.0803 mmol), cyclobutanone (11.3 mg, 0.161 mmol) and acetic acid (0.009 ml, 0.2 mmol) in 1,2-dichloroethane (0.8 ml) was stirred at room temperature for 20 h. After addition of sodium triacetoxyborohydride (37.4 mg, 0.177 mmol) the mixture was stirred for 1 h. Addition of methanol (0.5 ml) and N-ethyl diisopropylamine (0.028 ml, 0.16 mmol) to the reaction mixture was followed by concentration in vacuo. Preparative RP-HPLC with water (0.05% formic acid)/methanol as eluent gave the title compound (27 mg, 69%) as white solid. MS m/e: 490 ([M+H]+)

Workup

  1. concentrationwas followed by concentration in vacuo

Sources & evidence

ORD record
ord-6fc0e5775b104e26a6b69f1e08b9e951
Source dataset
uspto-grants-2013_07
Patent number
US08481528B2

Reaction notes

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