Sodium Hydroxide → (4-{2-[4-(2-Pyrrolidin-1-yl-ethoxy)-phenylamino]-[1,2,4]triazolo[1,5-a]pyridin-5-yl}-pyrazol-1-yl)-acetic acid

HRID 1054409Notes

Reaction equation

HRID 1054409 reaction equation
C[O:2][C:3](=[O:34])[CH2:4][N:5]1[CH:9]=[C:8]([C:10]2[N:15]3[N:16]=[C:17]([NH:19][C:20]4[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][N:29]5[CH2:33][CH2:32][CH2:31][CH2:30]5)=[CH:22][CH:21]=4)[N:18]=[C:14]3[CH:13]=[CH:12][CH:11]=2)[CH:7]=[N:6]1.[OH-].[Na+]>CO>[N:29]1([CH2:28][CH2:27][O:26][C:23]2[CH:24]=[CH:25][C:20]([NH:19][C:17]3[N:18]=[C:14]4[CH:13]=[CH:12][CH:11]=[C:10]([C:8]5[CH:7]=[N:6][N:5]([CH2:4][C:3]([OH:34])=[O:2])[CH:9]=5)[N:15]4[N:16]=3)=[CH:21][CH:22]=2)[CH2:30][CH2:31][CH2:32][CH2:33]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59589753(4-{2-[4-(2-Pyrrolidin-1-yl-ethoxy)-phenylamino]-[1,2,4]triazolo[1,5-a]pyridin-5-yl}-pyrazol-1-yl)-acetic acid methyl ester

Product 1

HCID 59589906(4-{2-[4-(2-Pyrrolidin-1-yl-ethoxy)-phenylamino]-[1,2,4]triazolo[1,5-a]pyridin-5-yl}-pyrazol-1-yl)-acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of (4-{2-[4-(2-pyrrolidin-1-yl-ethoxy)-phenylamino]-[1,2,4]triazolo[1,5-a]pyridin-5-yl}-pyrazol-1-yl)-acetic acid methyl ester (0.51 g, 1.1 lmmol) in methanol (10 ml) was added sodium hydroxide (2N, 1 mL) and the mixture stirred for 3 hours at room temperature. All solvents were removed in vacuo to afford the title compound as a pale yellow solid. No further purification was required. Yield: 0.40 g, 80%; LCMS method: 2, RT: 2.36 min, MI: 448 [M+1].

Workup

  1. customAll solvents were removed in vacuo

Sources & evidence

ORD record
ord-b09c87ce76474057b172943f03b77eba
Source dataset
uspto-grants-2016_07
Patent number
US09394301B2

Reaction notes

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