Carbamate → HCID 9984935, compound

HRID 1897446Notes

Reaction equation

HRID 1897446 reaction equation
[ClH:1].[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:4][C:3]([Cl:1])=[CH:10][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 9984935HCID 9984935, compound

Conditions

Temperature
80 °C

Procedure

A solution of (5t) (74 mg, 0.57 mmol) in DMF (1 mL) was treated with the corresponding carbamate (6t-2) (110 mg, 0.25 mmol) followed by DIEA (99 mL, 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. Desired fractions were evaporated in vacuo to provide the desired compound (7t-2) as a pale yellow oil (80 mg; 64% 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 547 (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. customDesired fractions were evaporated in vacuo
  9. customto provide

Sources & evidence

ORD record
ord-ea72aed5919a4113bc57a92c8c6aac93
Source dataset
uspto-grants-2013_08
Patent number
US08518983B2

Reaction notes

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