Water → HCID 67774995, compound

HRID 1037552Notes

Reaction equation

HRID 1037552 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([C:17](=[O:20])[NH:18][CH3:19])=[C:15]3[C:10]([CH:11]=[C:12]([N:24]([S:41]([CH3:44])(=[O:43])=[O:42])[CH2:25][CH2:26][CH2:27][NH:28][C:29](=[O:40])[CH2:30][CH2:31][NH:32]C(=O)OC(C)(C)C)[C:13]([CH:21]4[CH2:23][CH2:22]4)=[CH:14]3)=[N:9]2)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[K+].[K+].O>C(Cl)Cl>[NH2:32][CH2:31][CH2:30][C:29]([NH:28][CH2:27][CH2:26][CH2:25][N:24]([S:41]([CH3:44])(=[O:42])=[O:43])[C:12]1[C:13]([CH:21]2[CH2:22][CH2:23]2)=[CH:14][C:15]2[C:10]([CH:11]=1)=[N:9][N:8]([C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)[C:16]=2[C:17]([NH:18][CH3:19])=[O:20])=[O:40]

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 67962379HCID 67962379, compound

Product 1

HCID 67774995HCID 67774995, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of compound (ii) (20 mg, 0.029 mmol) and trifluoroacetic acid (50 uL) in DCM (0.5 mL) was stirred at 40° C. for 1 h. After cooling to RT, solid potassium carbonate (50 mg) was added and the mixture was stirred vigorously for 10 min. Water (0.5 mL) was then added and the organic phase was separated. The aqueous phase was extracted with DCM (1 mL) and the combined organics were dried (MgSO4) then concentrated in vacuo. The residue was purified by flash column chromatography eluting with MeOH/DCM (0-20%) to afford Compound (61) as a white solid (5.4 mg, 32%). ESI-MS m/z calculated for [M+H]+: 591.1/593.1; found: 591.1/593.1; 1H NMR (400 MHz, CDCl3) δ 7.74 (s, 1H), 7.69-7.60 (m, 2H), 7.50-7.42 (m, 2H), 7.35 (s, 1H), 7.24 (t, J=4.3 Hz, 1H), 5.95 (brd, J=4.6 Hz, 1H), 3.92-3.68 (m, 2H), 3.46-3.22 (m, 2H), 3.06 (s, 3H), 3.02-2.90 (m, 5H), 2.38 (tt, J=8.4, 5.4 Hz, 1H), 2.31-2.16 (m, 2H), 1.92-1.68 (m, 2H), 1.12-0.96 (m, 3H), 0.67-0.54 (m, 1H).

Workup

  1. temperatureAfter cooling to RT
  2. stirringthe mixture was stirred vigorously for 10 min
  3. customthe organic phase was separated
  4. extractionThe aqueous phase was extracted with DCM (1 mL)
  5. dry with materialthe combined organics were dried (MgSO4)
  6. concentrationthen concentrated in vacuo
  7. customThe residue was purified by flash column chromatography
  8. washeluting with MeOH/DCM (0-20%)

Sources & evidence

ORD record
ord-bdc2ee16f8724fb3a5b5cbbe482c31ee
Source dataset
uspto-grants-2013_10
Patent number
US08546389B2

Reaction notes

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