1,2-Dichloroethane → Hydrochloric Acid

HRID 1050524Notes

Reaction equation

HRID 1050524 reaction equation
[CH3:1][O:2][C:3]1[CH:39]=[CH:38][C:6]([C:7]([NH:9][C@@H:10]2[CH2:15][CH2:14][CH2:13][N:12]([C:16]3[N:17]=[C:18]([NH:25][C:26]4[CH:31]=[CH:30][C:29]([CH:32]5[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]5)=[CH:28][CH:27]=4)[C:19]([C:22]([NH2:24])=[O:23])=[N:20][CH:21]=3)[CH2:11]2)=[O:8])=[CH:5][CH:4]=1.CCN(C(C)C)[CH:43]([CH3:45])[CH3:44].CC(C)=O.C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[Cl:71]CCCl>O.O1CCOCC1>[CH:43]([N:35]1[CH2:36][CH2:37][CH:32]([C:29]2[CH:30]=[CH:31][C:26]([NH:25][C:18]3[C:19]([C:22]([NH2:24])=[O:23])=[N:20][CH:21]=[C:16]([N:12]4[CH2:13][CH2:14][CH2:15][C@@H:10]([NH:9][C:7](=[O:8])[C:6]5[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:39][CH:38]=5)[CH2:11]4)[N:17]=3)=[CH:27][CH:28]=2)[CH2:33][CH2:34]1)([CH3:45])[CH3:44].[ClH:71]

Participants

10

Reactant 6

HCID 111,2-DichloroethaneHCID 176Acetic AcidHCID 180AcetoneHCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 118133410HCID 118133410, compound

Product 2

HCID 313Hydrochloric AcidHCID 118115342HCID 118115342, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Compound 163 (70 mg, 0.12 mmol) was dissolved in 8 mL 1,2-dichloroethane and 8 mL dioxane with DIEA (105 μL, 0.60 mmol). To it was added acetone (180 μL, 2.4 mmol). The mixture was stirred at RT for 2 h. To it were added acetic acid (68 μL, 1.2 mmol) and then NaBH(OAc)3 (127 mg, 0.60 mmol). The mixture was stirred for overnight. It was diluted with 2 mL water, concentrated in vacuo, treated with TFA (0.2 mL) and subjected to reverse phase preparative HPLC to isolate (R)-3-(4-(1-isopropylpiperidin-4-yl)phenylamino)-5-(3-(4-methoxybenzamido)piperidin-1-yl)pyrazine-2-carboxamide (164) as HCl salt (34 mg). MS found for C32H41N7O3 as (M+H)+ 572.3, (M−H)− 570.4. UV: λ=258, 279, 305, 335, 372 nm.

Workup

  1. stirringThe mixture was stirred for overnight
  2. concentrationconcentrated in vacuo
  3. additiontreated with TFA (0.2 mL)

Sources & evidence

ORD record
ord-0ddfaa5f37fd4553aa7b9832766b4f2d
Source dataset
uspto-grants-2016_07
Patent number
US09382246B2

Reaction notes

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