Triethylamine → HCID 66887168, compound

HRID 75227Notes

Reaction equation

HRID 75227 reaction equation
FC(F)(F)C(O)=O.FC(F)(F)C(O)=O.[Cl:15][C:16]1[CH:17]=[C:18]([CH2:41]O)[CH:19]=[C:20]([Cl:40])[C:21]=1[C:22]1[NH:23][C:24]2[C:30]3[CH:31]=[CH:32][N:33]=[CH:34][C:29]=3[NH:28][C:27]3[N:35]=[CH:36][CH:37]=[CH:38][C:26]=3[C:25]=2[N:39]=1.C(N(CC)CC)C.S(Cl)([Cl:52])=O>C1(C)C=CC=CC=1.CO>[Cl:15][C:16]1[CH:17]=[C:18]([CH2:41][Cl:52])[CH:19]=[C:20]([Cl:40])[C:21]=1[C:22]1[NH:23][C:24]2[C:30]3[CH:31]=[CH:32][N:33]=[CH:34][C:29]=3[NH:28][C:27]3[N:35]=[CH:36][CH:37]=[CH:38][C:26]=3[C:25]=2[N:39]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 86613275[3,5-Dichloro-4-(3,8-dihydroimidazo[4,5-d]dipyrido[2,3-b:4',3'-f]azepin-2-yl)phenyl]methanol bis(trifluoroacetate)

Product 1

HCID 66887168HCID 66887168, compoundYield 67.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

To a solution of [3,5-dichloro-4-(3,8-dihydroimidazo[4,5-d]dipyrido[2,3-b:4′,3′-f]azepin-2-yl)phenyl]methanol bis(trifluoroacetate) (20.0 g, 0.03 mmol) in toluene (1.0 mL) was added triethylamine (11 μL, 0.08 mmol) and stirred for 5 minutes, followed by the addition of thionyl chloride (5.0 μL, 0.06 mmol) at room temperature for 16 hours. The reaction mixture was diluted with methanol and purified by preparative LCMS at pH 10 to give the desired product (8.7 mg, 65%). LC/MS: 428 (M+H)+.

Workup

  1. custompurified by preparative LCMS at pH 10

Sources & evidence

ORD record
ord-3af09b28b43f4b38ae7f135d9f2473e9
Source dataset
uspto-grants-2014_09
Patent number
US08835423B2

Reaction notes

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