Triethylamine → HCID 71138622, compound

HRID 1914024Notes

Reaction equation

HRID 1914024 reaction equation
Cl.Cl.Cl.Cl.[NH2:5][C:6]1([C:10]2[CH:15]=[CH:14][C:13]([N:16]3[C:20]4=[N:21][C:22]([C:25]5[CH:30]=[CH:29][CH:28]=[C:27]([N:31]6[CH2:36][CH2:35][CH:34]([NH2:37])[CH2:33][CH2:32]6)[CH:26]=5)=[CH:23][CH:24]=[C:19]4[N:18]=[C:17]3[C:38]3[C:39]([NH2:44])=[N:40][CH:41]=[CH:42][CH:43]=3)=[CH:12][CH:11]=2)[CH2:9][CH2:8][CH2:7]1.C(N(CC)CC)C.[CH3:52][S:53](Cl)(=[O:55])=[O:54]>C(Cl)Cl.CCOC(C)=O>[NH2:5][C:6]1([C:10]2[CH:11]=[CH:12][C:13]([N:16]3[C:20]4=[N:21][C:22]([C:25]5[CH:26]=[C:27]([N:31]6[CH2:32][CH2:33][CH:34]([NH:37][S:53]([CH3:52])(=[O:55])=[O:54])[CH2:35][CH2:36]6)[CH:28]=[CH:29][CH:30]=5)=[CH:23][CH:24]=[C:19]4[N:18]=[C:17]3[C:38]3[C:39]([NH2:44])=[N:40][CH:41]=[CH:42][CH:43]=3)=[CH:14][CH:15]=2)[CH2:7][CH2:8][CH2:9]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86675349HCID 86675349, compound

Product 1

HCID 71138622HCID 71138622, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-{3-[4-(1-aminocyclobutyl)phenyl]-5-[3-(4-aminopiperidin-1-yl)phenyl]-3H-imidazo[4,5-b]pyridin-2-yl}pyridin-2-amine tetrahydrochloride (49 mg, 0.0731 mmol) in CH2Cl2 (2 mL) was added triethylamine (0.061 mL, 0.439 mmol), then methanesulfonyl chloride (0.006 mL, 0.0804 mmol) at 0° C. and stirred at r.t for 3.5 hours. The mixture was diluted with AcOEt, washed with 0.5N NaOH, brine, dried over Na2SO4, then filtrated. The filtrate was concentrated and the residue was purified by preparative thin-layer chromatography (CH2Cl2/MeOH=5:1) to afford desired product (24 mg, 54%) as pale yellow solid.

Workup

  1. washwashed with 0.5N NaOH, brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltrated
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by preparative thin-layer chromatography (CH2Cl2/MeOH=5:1)

Sources & evidence

ORD record
ord-e24b725cd593421e9ebc9ce199fba39b
Source dataset
uspto-grants-2013_12
Patent number
US08609688B2

Reaction notes

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