Sodium Hydroxide → HCID 66799957, compound

HRID 528023Notes

Reaction equation

HRID 528023 reaction equation
[CH3:1][N:2]1[C:10]([C:11]([OH:13])=[O:12])=[N:9][C:8]2[C:3]1=[N:4][CH:5]=[N:6][C:7]=2[N:14]1[CH2:19][CH2:18][CH:17]([N:20]2[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[NH:22][C:21]2=[O:29])[CH2:16][CH2:15]1.[CH:30]1(N2C3N=CN=C(N4CCC(N5C6C=CC=CC=6NC5=O)CC4)C=3N=C(OC)C2=O)C[CH2:31]1.[OH-].[Na+]>CO>[CH:1]1([N:2]2[C:10]([C:11]([OH:13])=[O:12])=[N:9][C:8]3[C:3]2=[N:4][CH:5]=[N:6][C:7]=3[N:14]2[CH2:19][CH2:18][CH:17]([N:20]3[C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=4[NH:22][C:21]3=[O:29])[CH2:16][CH2:15]2)[CH2:31][CH2:30]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 66799891HCID 66799891, compoundHCID 66799955HCID 66799955, compound

Product 1

HCID 66799957HCID 66799957, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

9-Cyclopropyl-6-[4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl]-9H-purine-8-carboxylic acid was prepared in the same manner as 9-methyl-6-[4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl]-9H-purine-8-carboxylic acid. The 8-cyclopropyl-6-methoxy-4-[4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl]pteridin-7(8H)-one (0.836 g, 1.93 mmol) was treated with 2M sodium hydroxide (10 mL, 20 mmol) in methanol at 80° C. for 18 hours gave 0.789 of 9-cyclopropyl-6-[4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl]-9H-purine-8-carboxylic acid as an off-white solid. 1H NMR (400 MHz, DMSO-d6): δ 11.20 (br s, 1H), 8.07 (s, 1H), 6.93 (m, 1H), 6.71 (m, 3H), 5.19 (broad s, 2H), 4.27 (m, 1H), 3.40 (m, 2H), 3.19 (t, 2H), 2.43 (m, 2H), 1.82 (d, 2H), 1.15 (m, 2H), 0.84 (m, 2H). MS (EI) for C21H21N7O4: 420 (MH+).

Sources & evidence

ORD record
ord-66155002b44b49178e6c1c87c50a5110
Source dataset
uspto-grants-2016_05
Patent number
US09346807B2

Reaction notes

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