Triethylamine → HCID 178500484, compound

HRID 1108274Notes

Reaction equation

HRID 1108274 reaction equation
I[C:2]1[N:3]([C:21]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:4]=[C:5]([C:7]([NH:9][C@H:10]([C:17]([O:19][CH3:20])=[O:18])[CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[O:8])[N:6]=1.[C:40]([NH:46][C:47]1[N:48]=[C:49]([OH:59])[C:50]2[CH:56]=[C:55]([C:57]#[CH:58])[CH:54]=[N:53][C:51]=2[N:52]=1)(=[O:45])[C:41]([CH3:44])([CH3:43])[CH3:42].C(N(CC)CC)C>C(#N)C>[C:40]([NH:46][C:47]1[N:48]=[C:49]([OH:59])[C:50]2[CH:56]=[C:55]([C:57]#[C:58][C:2]3[N:3]([C:21]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:4]=[C:5]([C:7]([NH:9][C@H:10]([C:17]([O:19][CH3:20])=[O:18])[CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[O:8])[N:6]=3)[CH:54]=[N:53][C:51]=2[N:52]=1)(=[O:45])[C:41]([CH3:44])([CH3:43])[CH3:42]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 54180859dimethyl N-(2-iodo-1-triphenylmethylimidazol-4-ylcarbonyl)-L-glutamateHCID 178437079HCID 178437079, compound

Product 1

HCID 178500484HCID 178500484, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Following the procedure of Example 1, dimethyl N-(2-iodo-1-triphenylmethylimidazol-4-ylcarbonyl)-L-glutamate (638 mg, 1.0 mmol), 2-pivaloylamino4-hydroxy-6-ethynylpyrido[2,3-d]pyrimidine (541 mg, 2.0 mmol), Pd(PPh)2Cl2 (35 mg, 0.05 mmol), cuprous iodide (19 mg, 0.1 mmol), triethylamine (0.7 mL), and acetonitrile (50 mL) yield dimethyl N-(2-[2-(2-pivaloylamino-4-hydroxypyrido[2,3-d]pyrimidin-6-yl)ethynyl]-1-triphenylmethylimidazol-4-ylcarbonyl}-L-glutamate [515 mg, 66% after flash column chromatography (ethyl acetate:hexanes, 2:1), mp 93-95° C]: 1H NMR (CDCl3) δ 12.05 (br s, 1H), 8.43 (br s, 1H), 8.26 (s, 1H), 7.93 (d, 1H, J=2.2 Hz), 7.61 (s, 1H), 7.54 (d, 1H, J=7.6 Hz), 7.33-7.28 (m, 9H), 7.18-7.12 (m, 6H), 4.77 (m, 1H), 3.74 (s, 3H), 3.65 (s, 3H), 2.45 (m, 2H), 2.32 (m, 1H), 2.05 (m, 1H), 1.30 (s, 9H). HRMS calcd for C44H41N7O7 779.3067, found 779.3088.

Sources & evidence

ORD record
ord-f4e79b7f8e8b4066ac9807c65bd27cdd
Source dataset
uspto-grants-2000_05
Patent number
US06066639

Reaction notes

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