Dimethylamine → HCID 68505534, compound

HRID 1714050Notes

Reaction equation

HRID 1714050 reaction equation
FC(F)(F)C([O-])=O.[C:8]([C:11]1[CH:12]=[CH:13][C:14]2[C:15]([CH:31]3[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]3)=[C:16]3[C:23]4[CH:24]=[CH:25][C:26]([F:28])=[CH:27][C:22]=4[CH2:21][NH2+:20][CH2:19][CH2:18][N:17]3[C:29]=2[CH:30]=1)([OH:10])=[O:9].Cl[CH2:38][CH2:39][S:40](Cl)(=[O:42])=[O:41].C[CH2:45][N:46](CC)[CH2:47]C.CNC.C1COCC1>C(Cl)Cl.CN(C=O)C.CC#N>[CH:31]1([C:15]2[C:14]3[CH:13]=[CH:12][C:11]([C:8]([OH:10])=[O:9])=[CH:30][C:29]=3[N:17]3[CH2:18][CH2:19][N:20]([S:40]([CH2:39][CH2:38][N:46]([CH3:47])[CH3:45])(=[O:42])=[O:41])[CH2:21][C:22]4[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=4[C:16]=23)[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]1

Participants

9

Reactant 5

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 86604969HCID 86604969, compound

Product 1

HCID 68505534HCID 68505534, compoundYield 16%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1 eq of 11-carboxy-14-cyclohexyl-3-fluoro-5,6,7,8-tetrahydroindolo[2,1-a][2,5]benzodiazocin-6-ium trifluoroacetate (prepared as described in Example 44, Step 1) in DCM (plus some drops of MeCN and DMF) (0.08 M) was added to a solution of 1.1 eq of 2-chloro-ethansulfonyl chloride in DCM (0.08 M) and 2.2 eq of Et3N and the mixture stirred at RT for 5 mins. At which time a solution of dimethylamine 2 M in THF (5 eq) was added and the mixture stirred at RT overnight. Volatiles were removed in vacuo. The crude was then purified by automated RP-MS-HPLC (stationary phase: column Waters SYMMETRY prep. C18, 7 μm, 19×300 mm. Mobile phase: MeCN/H2O buffered with 0.1% TFA). Fractions containing the pure compound were combined and freeze dried to afford the title compound as a white powder (16%).

Workup

  1. stirringthe mixture stirred at RT overnight
  2. customVolatiles were removed in vacuo
  3. customThe crude was then purified by automated RP-MS-HPLC (stationary phase: column Waters SYMMETRY prep. C18, 7 μm, 19×300 mm. Mobile phase: MeCN/H2O buffered with 0.1% TFA)
  4. additionFractions containing the pure compound
  5. customfreeze dried

Sources & evidence

ORD record
ord-a250445aebca46958d0337d63cb2cf5f
Source dataset
uspto-grants-2010_09
Patent number
US07795247B2

Reaction notes

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