Carbamate → HCID 42641987, compound

HRID 1897445Notes

Reaction equation

HRID 1897445 reaction equation
Cl.[F:2][C:3]1[CH:4]=[CH:5][C:6]([O:11][C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[N:17]([CH3:21])[N:16]=[CH:15]3)=[C:7]([CH:10]=1)[CH2:8][NH2:9].[C:22](=[O:25])([O-])[NH2:23].CC[N:28]([CH:32]([CH3:34])C)[CH:29]([CH3:31])[CH3:30].C[N:36]([CH:38]=O)C>>[C:14]([C:38]1[CH:34]=[C:32]([NH:23][C:22]([NH:9][CH2:8][C:7]2[CH:10]=[C:3]([F:2])[CH:4]=[CH:5][C:6]=2[O:11][C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[N:17]([CH3:21])[N:16]=[CH:15]3)=[O:25])[N:28]([C:29]2[CH:30]=[CH:8][C:7]([CH3:10])=[CH:6][CH:31]=2)[N:36]=1)([CH3:18])([CH3:15])[CH3:13]

Participants

5

Reactant 4

HCID 276CarbamateHCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 57484115HCID 57484115, compound

Product 1

HCID 42641987HCID 42641987, compound

Conditions

Temperature
80 °C

Procedure

A solution of (5t) (70 mg, 0.23 mmol) in DMF (1 mL) was treated with the corresponding carbamate (6t-1) (100 mg, 0.25 mmol) followed by DIEA (99 μL, 0.57 mmol). The mixture was heated at 80° C. for 18 hours under nitrogen purge. The solvent was evaporated in vacuo and the residue taken up in DCM and washed with 1N HCl. The organic layer was filtered through 1PS paper and evaporated in vacuo to an oil that was purified on a silica gel SepPak cartridge eluting with 10:1 DCM/Et2O. The desired fractions were evaporated in vacuo to provide the desired compound (7t-1) as a pale yellow oil (80 mg; 67% isolated yield). 1H NMR (400 MHz, CDCl3) δ 7.38 (d, J=7.8 Hz, 1H), 7.17 (dd, J=7.8, 1.6 Hz, 1H), 7.13 (d, J=1.6 Hz, 1H), 5.19-5.18 (m, 1H), 4.51-4.44 (m, 1H), 4.43-4.36 (m, 1H), 2.53-2.45 (m, 1H), 2.36-2.30 (m, 1H); MS (ESI+) m/z 527 (M+H) detected.

Workup

  1. custompurge
  2. customThe solvent was evaporated in vacuo
  3. washwashed with 1N HCl
  4. filtrationThe organic layer was filtered through 1PS paper
  5. customevaporated in vacuo to an oil that
  6. customwas purified on a silica gel SepPak cartridge
  7. washeluting with 10:1 DCM/Et2O
  8. customThe desired fractions were evaporated in vacuo
  9. customto provide

Sources & evidence

ORD record
ord-b201adf5e1ef440db7c6999158f453af
Source dataset
uspto-grants-2013_08
Patent number
US08518983B2

Reaction notes

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