Sodium Hydroxide → HCID 178508895, compound

HRID 1108280Notes

Reaction equation

C([NH:7][C:8]1[N:9]=[C:10]([OH:39])[C:11]2[CH2:17][CH:16]([CH2:18][CH2:19][C:20]3[NH:21][CH:22]=[C:23]([C:25]([NH:27][C@H:28]([C:35]([O:37]C)=[O:36])[CH2:29][CH2:30][C:31]([O:33]C)=[O:32])=[O:26])[N:24]=3)[CH2:15][NH:14][C:12]=2[N:13]=1)(=O)C(C)(C)C.[OH-].[Na+]>>[NH2:7][C:8]1[N:9]=[C:10]([OH:39])[C:11]2[CH2:17][CH:16]([CH2:18][CH2:19][C:20]3[NH:21][CH:22]=[C:23]([C:25]([NH:27][C@H:28]([C:35]([OH:37])=[O:36])[CH2:29][CH2:30][C:31]([OH:33])=[O:32])=[O:26])[N:24]=3)[CH2:15][NH:14][C:12]=2[N:13]=1

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 178500485HCID 178500485, compound

Product 1

HCID 178508895HCID 178508895, compoundYield 44%

Procedure

Dimethyl N-{2-[2-(2-pivaloylamino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]-pyrimidin-6-yl)ethyl]imidazol-4-ylcarbonyl}-L-glutamate (109 mg g, 0.2 mmol) and 0.5N sodium hydroxide (1 mL) are allowed to react analogously to the method described in Example 19 to yield N-{2-[2-(amino-4-hydroxy-5,6,7,8-tetrahydropyrido-[2,3-d]pyrimidin-6-yl)ethyl]imidazol-4-ylcarbonyl}-L-glutamic acid (38 mg, 44%, mp >260° C.): 1H NMR (DMSOd6) d 12.35 (br s, 1H), 12.21 (br s, 1H), 9.77 (br s, 1H), 7.80 (br s, 1H), 7.50 (s, 1H), 6.27 (s, 1H), 5.92 (s, 2H), 4.37 (m, 1H), 3.17 (br d, 1H, J=10.6 Hz), 2.79-2.61 (m, 3H), 2.44 (m, 1H), 2.26 (m, 2H), 2.07-1.76 (m, 3 H), 1.68-1.59 (m, 3H).

Workup

customto react analogously to the method

Sources & evidence

ORD record: ord-f90c14f50a0240b4a7a1ad8538893aee
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06066639

Reaction notes

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