Lithium Hydroxide → 3-{4-[3 (R)-Amino-piperidin-1-yl]-3-(2-cyano-benzyl)-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-ylmethyl}-benzoic acid

HRID 2193427Notes

Reaction equation

HRID 2193427 reaction equation
C[O:2][C:3](=[O:35])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][N:11]2[C:16](=[O:17])[CH:15]=[C:14]([N:18]3[CH2:23][CH2:22][CH2:21][C@@H:20]([NH2:24])[CH2:19]3)[N:13]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]#[N:33])[C:12]2=[O:34])[CH:5]=1.[Li+].[OH-]>C1COCC1.O>[NH2:24][C@@H:20]1[CH2:21][CH2:22][CH2:23][N:18]([C:14]2[N:13]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]#[N:33])[C:12](=[O:34])[N:11]([CH2:10][C:6]3[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=3)[C:3]([OH:35])=[O:2])[C:16](=[O:17])[CH:15]=2)[CH2:19]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 112944223-{4-[3(R)-Amino-piperidin-1-yl]-3-(2-cyano-benzyl)-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-ylmethyl}-benzoic acid methyl ester

Product 1

HCID 114425273-{4-[3 (R)-Amino-piperidin-1-yl]-3-(2-cyano-benzyl)-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-ylmethyl}-benzoic acid

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A crude mixture of compound 24 (˜50 mg) was treated with LiOH in THF-water (10:1) to give the title compound 25. 1H-NMR (400 MHz, CDCl3-CD3OD 10:1) δ 7.90 (s, 1H), 7.86 (d, J=7.6 Hz, 1H), 7.60 (d, J=7.6 Hz, 1H), 7.50 (t, J=8.2 Hz, 1H), 7.45 (d, J=7.3 Hz, 1H), 7.26-7.36 (m, 2H), 7.17 (d, J=8.1 Hz, 1H), 5.39 (s, 1H), 5.10-5.25 (ABq, J=36.9, 15.5 Hz, 2H), 5.03 (s, 2H), 3.31 (m, 2H), 2.95 (m, 1H), 2.81 (m, 1H), 2.64 (m, 1H), 2.07 (m, 1H), 1.82 (m, 1H), 1.51-1.68 (m, 2H). MS (ES) [m+H] calc'd for C25H26N5O4, 460.2. found 460.2.

Sources & evidence

ORD record
ord-100465eca5284e109b96e2e85f7ce3bc
Source dataset
uspto-grants-2012_12
Patent number
US08329900B2

Reaction notes

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