Potassium Phosphate, Tribasic → HCID 178453615, compound

HRID 1259440Notes

Reaction equation

HRID 1259440 reaction equation
[C:1]([O:5][C:6](=[O:32])[NH:7][CH2:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15](=[O:31])[NH:16][CH:17]([C:25]2[S:26][CH:27]=[C:28](Br)[CH:29]=2)[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].[C:33]([C:36]1[CH:41]=[CH:40][C:39](B(O)O)=[CH:38][CH:37]=1)(=[O:35])[NH2:34].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.[Pd].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>[C:1]([O:5][C:6](=[O:32])[NH:7][CH2:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15](=[O:31])[NH:16][CH:17]([C:25]2[S:26][CH:27]=[C:28]([C:39]3[CH:40]=[CH:41][C:36]([C:33](=[O:35])[NH2:34])=[CH:37][CH:38]=3)[CH:29]=2)[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 27378114-Aminocarbonylphenylboronic acidHCID 178453613HCID 178453613, compound

Product 1

HCID 178453615HCID 178453615, compound

Reagents, catalysts & solvents 2

HCID 2734558Bis(tri-tert-butylphosphine)palladium(0)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 1B (522 mg, 1.0 mmol) and 4-carbamoylphenylboronic acid (248 mg, 1.5 mmol) was dissolved in DMF (15 mL). Under N2, potassium phosphate (530 mg, 2.5 mmol) and bis(tri-t-butylphosphine) palladium (25 mg, 5 mol %) were added to the mixture. The resulting mixture was stirred at 85° C. for 2.5 h. The reaction mixture was cooled to rt, filtered and concentrated. Reverse-phase HPLC purification afforded IC as a light yellow solid. LC/MS m/z 561.2 (M+H)+. 1H NMR (400 MHz, CD3OD) δ: 0.91-0.95 (m, 2H), 1.29-1.42 (m, 4H), 1.55-1.63, (m, 1H), 1.75-1.78 (m, 2H), 1.98-2.09 (m, 1H), 2.85 (d, J=7.9 Hz, 2H), 3.30-3.33 (m, 2H), 5.45-5.48 (m, 1H), 7.19-7.20 (m, 1H), 7.25, (s, 4H), 7.35 (s, 1H), 7.61 (s, 1H), 7.69 (d, J=7.6 Hz, 2H), 7.87 (d, J=7.6 Hz, 2H), 7.97 (s, 1H), 8.41 (m, 1H).

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customReverse-phase HPLC purification
  5. customafforded IC as a light yellow solid

Sources & evidence

ORD record
ord-4b91012cb62644168249084d2d6e4d9a
Source dataset
uspto-grants-2013_06
Patent number
US08466295B2

Reaction notes

Loading…