Trifluoroacetic acid → HCID 178510436, compound

HRID 1711281Notes

Reaction equation

HRID 1711281 reaction equation
[C:1]1([C:7]2[CH:12]=[C:11]([S:13]([N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)(=[O:15])=[O:14])[CH:10]=[CH:9][C:8]=2[NH:22][C:23]([C:25]2[N:26](COCC[Si](C)(C)C)[CH:27]=[C:28]([C:30]#[N:31])[N:29]=2)=[O:24])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl.CO>[C:1]1([C:7]2[CH:12]=[C:11]([S:13]([N:16]3[CH2:17][CH2:18][O:19][CH2:20][CH2:21]3)(=[O:14])=[O:15])[CH:10]=[CH:9][C:8]=2[NH:22][C:23]([C:25]2[NH:26][CH:27]=[C:28]([C:30]#[N:31])[N:29]=2)=[O:24])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58754879HCID 58754879, compound

Product 1

HCID 178510436HCID 178510436, compoundYield 29.4%

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 15.0 mg (0.0262 mmol) of 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [2-cyclohex-1-enyl-4-(morpholine-4-sulfonyl)-phenyl]-amide (as prepared in the previous step) in CH2Cl2 (5 mL) was treated with MeOH (1 drop) and TFA (1 mL). The mixture was stirred at RT for 2 h, and the solvents were evaporated in vacuo. Purification of the residue by RP-HPLC (C18) with 10-80% CH3CN in 0.1% TFA/H2O over 30 min afforded 3.4 mg (29%) of the title compound as a white solid: 1H-NMR (CD3OD; 400 MHz): δ 8.62 (d, 1H, J=8.8 Hz), 8.07 (s, 1H), 7.72 (dd, 1H, J=8.8, 2.0 Hz), 7.57 (d, 1H, J=2.0 Hz), 6.01-5.96 (m, 1H), 3.77-3.70 (m, 4H), 3.02-2.95 (m, 4H), 2.40-2.30 (m, 4H), 1.97-1.82 (m, 4H). Mass spectrum (ESI, m/z): Calcd. for C21H23N5O4S, 442.2 (M+H), found 441.9.

Workup

  1. customthe solvents were evaporated in vacuo
  2. customPurification of the residue by RP-HPLC (C18) with 10-80% CH3CN in 0.1% TFA/H2O over 30 min

Sources & evidence

ORD record
ord-6007a1346dcf4754a83dde59d6cc5d2d
Source dataset
uspto-grants-2010_09
Patent number
US07790724B2

Reaction notes

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