Ethanol → HCID 11691812, compound

HRID 2367824Notes

Reaction equation

HRID 2367824 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]([C:23]3[N:27]=[C:26]([Cl:28])[N:25](COCC[Si](C)(C)C)[N:24]=3)=[O:22])=[C:16]([C:37]3[CH2:42][CH2:41][CH2:40][CH2:39][CH:38]=3)[CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.CCO.[C:46]([OH:52])([C:48]([F:51])([F:50])[F:49])=[O:47]>C(Cl)Cl>[F:49][C:48]([F:51])([F:50])[C:46]([OH:52])=[O:47].[C:37]1([C:16]2[CH:15]=[C:14]([CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[CH:19]=[CH:18][C:17]=2[NH:20][C:21]([C:23]2[N:27]=[C:26]([Cl:28])[NH:25][N:24]=2)=[O:22])[CH2:42][CH2:41][CH2:40][CH2:39][CH:38]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 6422Trifluoroacetic acid2×HCID 59128587HCID 59128587, compound

Product 1

HCID 11691812HCID 11691812, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(4-{[5-chloro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-[1,2,4]-triazole-3-carbonyl]-amino}-3-cyclohex-1-enyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (as prepared in the previous step, 63.3 mg, 0.102 mmol) in DCM (0.5 mL) and EtOH (11 μL) was added TFA (0.1 mL). After stirring the resulting mixture at RT for 12 h, another 0.11 mL of TFA was added. The reaction mixture was stirred for an additional 5 h at RT, the solvents were evaporated, and the title compound was purified by RP-HPLC (C18) eluting with 20-70% CH3CN in 0.1% TFA/H2O over 20 min to obtain the title compound (30 mg, 58%). 1H-NMR (CD3OD; 400 MHz): δ 8.14 (d, 1H, J=8.4 Hz), 7.20 (dd, 1H, J=8.4, 2.1 Hz), 7.13 (d, 1H, J=2.1 Hz), 5.82 (br s, 1H), 3.45 (m, 2H), 3.19 (m, 2H), 2.98 (m, 1H), 2.28 (m, 4H), 2.14 (m, 2H), and 1.95-1.75 (m, 6H). Mass spectrum (ESI, m/z): Calcd. for C20H24ClN5O, 386.1 and 388.1 (M+H). found 386.2 and 388.1.

Workup

  1. stirringThe reaction mixture was stirred for an additional 5 h at RT
  2. customthe solvents were evaporated
  3. customthe title compound was purified by RP-HPLC (C18)
  4. washeluting with 20-70% CH3CN in 0.1% TFA/H2O over 20 min

Sources & evidence

ORD record
ord-76845847cd9e45dd808a270aeb363e90
Source dataset
uspto-grants-2014_04
Patent number
US08697716B2

Reaction notes

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