Ammonium Hydroxide → HCID 10184407, compound

HRID 456702Notes

Reaction equation

HRID 456702 reaction equation
[CH:1]1([NH:6][C:7]2[C:8]3[N:9]([C:13]([C:24]4[CH:29]=[CH:28][N:27]=[C:26]([NH:30][CH:31]5[CH2:35][CH2:34][CH2:33][CH2:32]5)[N:25]=4)=[C:14]([C:16]4[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=4)[N:15]=3)[CH:10]=[CH:11][CH:12]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-:36].[NH4+].[O:38]1CCCC1.C[OH:44]>>[OH:36][OH:44].[CH:1]1([NH:6][C:7]2[C:8]3[N:9]([C:13]([C:24]4[CH:29]=[CH:28][N:27]=[C:26]([NH:30][CH:31]5[CH2:35][CH2:34][CH2:33][CH2:32]5)[N:25]=4)=[C:14]([C:16]4[CH:17]=[CH:18][C:19]([C:20]([NH2:21])=[O:38])=[CH:22][CH:23]=4)[N:15]=3)[CH:10]=[CH:11][CH:12]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 10276554HCID 10276554, compoundHCID 21899815MeOH tetrahydrofuran

Product 2

HCID 784Hydrogen PeroxideHCID 10184407HCID 10184407, compoundYield 52%

Procedure

In a similar manner as described in Example 28 from 4-{8-(cyclopentylamino)-3-[2-(cyclopentylamino)-4-pyrimidinyl]imidazo[1,2-α]pyridin-2-yl}benzonitrile (15 mg, 0.03 mmol), ammonium hydroxide, and hydrogen peroxide in tetrahydrofuran/methanol was formed 4-{8-(cyclopentylamino)-3-[2-(cyclopentylamino)-4-pyrimidinyl]imidazo[1,2-α]pyridin-2-yl}benzamide (8 mg, 52%) as a yellow solid. 1H NMR (CDCl3): δ 8.76 (broad, 1H), 8.12 (d, 1H), 7.88 (d, 2H), 7.81 (d, 2H), 6.82 (t, 1H), 6.40 (d, 1H), 6.31 (d, 1H), 5.27 (m, 2H), 4.38 (m, 1H), 3.97 (m, 1H), 2.19–2.10 (m, 4H), 1.84–1.58 (m, 12H); MS m/z 482 (M+1).

Sources & evidence

ORD record
ord-2d1dcb3e7e8a46e68eeb27d186cf90f9
Source dataset
uspto-grants-2007_03
Patent number
US07186714B2

Reaction notes

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