Potassium Carbonate → HCID 57563207, compound

HRID 1726235Notes

Reaction equation

HRID 1726235 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([F:39])=[C:7]([CH:38]=1)[CH2:8][N:9]([C:31]1[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=1)[CH:10]1[CH2:15][CH2:14][N:13]([C@H:16]([CH3:30])[CH2:17][CH2:18][NH:19][C:20]([C:22]2[C:23]([CH3:29])=[N:24][CH:25]=[N:26][C:27]=2[CH3:28])=[O:21])[CH2:12][CH2:11]1)#[N:2].Br[CH2:41][C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:45]([O:44][C:42](=[O:43])[CH2:41][O:37][C:34]1[CH:33]=[CH:32][C:31]([N:9]([CH2:8][C:7]2[CH:38]=[C:3]([C:1]#[N:2])[CH:4]=[CH:5][C:6]=2[F:39])[CH:10]2[CH2:11][CH2:12][N:13]([C@H:16]([CH3:30])[CH2:17][CH2:18][NH:19][C:20]([C:22]3[C:27]([CH3:28])=[N:26][CH:25]=[N:24][C:23]=3[CH3:29])=[O:21])[CH2:14][CH2:15]2)=[CH:36][CH:35]=1)([CH3:48])([CH3:47])[CH3:46]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 57563051HCID 57563051, compound

Product 1

HCID 57563207HCID 57563207, compoundYield 72.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of COMPOUND 233 (100 mg, 0.188 mmol), t-butyl bromoacetate (37 mg, 0.19 mmol) and K2CO3 (39 mg, 0.28 mmol) in DMF (1.9 mL) were heated at 80° C. for 18 h to give COMPOUND 235 as a yellow foam (88 mg, 72%) following work-up and purification. 1H NMR (CDCl3) δ 0.92-1.03 (m, 1H), 1.01 (d, 3H, J=6.6 Hz), 1.08-1.20 (m, 1H), 1.46 (s, 9H), 1.52-1.63 (m, 1H), 1.76 (m, 3H), 2.16 (m, 1H), 2.50 (s, 6H), 2.54 (m, 1H), 2.68-2.95 (m, 3H), 3.31-3.46 (m, 2H), 3.82 (m, 1H), 3.92 (s, 2H), 4.41 (s, 2H), 6.58 (m, 2H), 6.73 (m, 2H), 7.16 (m, 1H), 7.51 (m, 2H), 8.30 (m, 1H), 8.83 (s, 1H). ES-MS m/z 645 (M+H).

Sources & evidence

ORD record
ord-c9bdcc4e50c34e6189449fe8c2b609f0
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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