Dimethylcarbamoyl Chloride → Trifluoroacetic acid

HRID 712132Notes

Reaction equation

HRID 712132 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].FC(F)(F)C(O)=O.[NH2:15][CH2:16][C@H:17]1[CH2:22][CH2:21][C@H:20]([N:23]2[C:27]3=[C:28]4[S:34][CH:33]=[CH:32][C:29]4=[N:30][CH:31]=[C:26]3[N:25]=[C:24]2[C@H:35]([OH:37])[CH3:36])[CH2:19][CH2:18]1.C(N(CC)CC)C.[CH3:45][N:46]([CH3:50])[C:47](Cl)=[O:48]>C(Cl)Cl>[OH:37][C@@H:35]([C:24]1[N:23]([C@H:20]2[CH2:21][CH2:22][C@H:17]([CH2:16][NH:15][C:47](=[O:48])[N:46]([CH3:50])[CH3:45])[CH2:18][CH2:19]2)[C:27]2=[C:28]3[S:34][CH:33]=[CH:32][C:29]3=[N:30][CH:31]=[C:26]2[N:25]=1)[CH3:36].[C:3]([OH:5])([C:2]([F:7])([F:6])[F:1])=[O:4]

Participants

6

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 178462243HCID 178462243, compound

Product 2

HCID 6422Trifluoroacetic acidYield 102.8%HCID 178462244HCID 178462244, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1R)-1-{1-[trans-4-(aminomethyl)cyclohexyl]-1H-imidazo[4,5-d]thieno[3,2-b]pyridin-2-yl}ethanol bis(trifluoroacetate) (16 mg, 0.029 mmol) and triethylamine (20 μL, 0.14 mmol) in methylene chloride (1 mL) was added N,N-dimethylcarbamoyl chloride (3.2 μL, 0.034 mmol). The mixture was stirred at room temperature for 1 h, then stripped to dryness and purified on prep-LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.05% TFA, at flow rate of 60 mL/min) to give the desired compound as TFA salt (3.4 mg, 30%) as TFA salt. LCMS calculated for C20H28N5O2S (M+H)+: m/z=402.2. Found: 402.2.

Workup

  1. custompurified on prep-LCMS (XBridge C18 column
  2. washeluting with a gradient of acetonitrile/water containing 0.05% TFA, at flow rate of 60 mL/min)

Sources & evidence

ORD record
ord-0c77e107d32148898c642f483bddbdad
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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