Acetic Acid → HCID 44194822, compound

HRID 1878605Notes

Reaction equation

HRID 1878605 reaction equation
C[O:2][C:3](=[O:35])[CH2:4][NH:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:14]=[N:15][CH:16]=[C:17]([C:19]3[CH:24]=[C:23]([C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[N:26]=4)[N:22]=[C:21]4[NH:32][CH:33]=[CH:34][C:20]=34)[CH:18]=2)=[CH:9][CH:8]=1.[OH-].[Na+].O.CC(O)=O>CO>[CH3:31][C:27]1[N:26]=[C:25]([C:23]2[N:22]=[C:21]3[NH:32][CH:33]=[CH:34][C:20]3=[C:19]([C:17]3[CH:18]=[C:13]([C:10]4[CH:11]=[CH:12][C:7]([CH2:6][NH:5][CH2:4][C:3]([OH:35])=[O:2])=[CH:8][CH:9]=4)[CH:14]=[N:15][CH:16]=3)[CH:24]=2)[CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 44193862HCID 44193862, compound

Product 1

HCID 44194822HCID 44194822, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (4-{5-[6-(6-methyl-pyridin-2-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-pyridin-3-yl}-benzylamino)-acetic acid methyl ester (Example 133) (1 eq, 0.216 mmol, 100 mg) in MeOH (10 ml) is added aqueous NaOH solution (1 M, 25 eq, 5.39 mmol, 5.39 ml). The resulting mixture is stirred for 1 h at r.t. Water is added, then the mixture is adjusted to pH 4 using AcOH, then washed with DCM/isopropanol (3:1). The aqueous layer is concentrated in vacuo, and the remaining residue is purified by column chromatography (DCM/MeOH/NH3) and subsequent reversed phase HPLC giving the title compound; [M+H]+=450; 1H-NMR (400 MHz, CD3OD): δ 9.01 (m, 1H), 8.92 (m, 1H), 8.52 (m, 1H), 8.31 (d, 1H), 8.25 (s, 1H), 7.98-7.87 (m, 3H), 7.69-7.62 (m, 3H), 7.40 (d, 1H), 6.73 (d, 1H), 4.32 (s, 2H), 3.70 (s, 2H), 2.69 (s, 3H).

Workup

  1. washwashed with DCM/isopropanol (3:1)
  2. concentrationThe aqueous layer is concentrated in vacuo
  3. customthe remaining residue is purified by column chromatography (DCM/MeOH/NH3) and subsequent reversed phase HPLC

Sources & evidence

ORD record
ord-9ae18e58a118449e8f590a50a0bd4162
Source dataset
uspto-grants-2012_11
Patent number
US08314112B2

Reaction notes

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