Dimethyl 4-ethynylbenzoylglutamate → HCID 178500481, compound

HRID 2226017Notes

Reaction equation

HRID 2226017 reaction equation
I[N:2]1[C:7]([OH:8])=[C:6]2[CH:9]=[CH:10][N:11]=[C:5]2[N:4]=[CH:3]1.[C:12]([C:14]1[CH:33]=[CH:32][C:17]([C:18]([NH:20][C@H:21]([C:28]([O:30][CH3:31])=[O:29])[CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])=[O:19])=[CH:16][CH:15]=1)#[CH:13]>>[OH:8][C:7]1[N:2]([C:13]#[C:12][C:14]2[CH:15]=[CH:16][C:17]([C:18]([NH:20][C@H:21]([C:28]([O:30][CH3:31])=[O:29])[CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])=[O:19])=[CH:32][CH:33]=2)[CH:3]=[N:4][C:5]2=[N:11][CH:10]=[CH:9][C:6]=12

Participants

3

Reactant 2

HCID 15024200Dimethyl 4-ethynylbenzoylglutamateHCID 178515134HCID 178515134, compound

Product 1

HCID 178500481HCID 178500481, compound

Procedure

By allowing 3-iodo-4-hydroxypyrrolo[2,3-d]pyrimidine to react with dimethyl N-(4-ethynylbenzoyl)-L-glutamate in the manner described in Example 2, there is obtained dimethyl N-[4-(4-hydroxypyrrolo[2,3-d]pyrimidin-3-ylethynyl)benzoyl]-L-glutamate which is purified by chromatography over silica, m.p. 160 ° C. (dec.). 1NMR (d6 -DMSO)δ1.98-2.15 (m, 2H), 2.45 (t, J=7.5 Hz, 2H) 3.57 (s, 3H), 3.64 (s, 3H), 4.40-4.45 (m, 1H), 7.51 ((d, J=2.5 Hz, 1H), 7.55 (d, J=8.2 Hz, 2 H), 7.87 (s, 1H), 7.90 (d, J=8.2 Hz, 1 H), 11.97 ((d, J=3.7 Hz, 1 H), 12.31 (s, 1H).

Sources & evidence

ORD record
ord-1a73133c39e14a2597a3557548b65ffe
Source dataset
uspto-grants-1994_09
Patent number
US05344932

Reaction notes

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