Methanol → (2-chloro-6-fluoro-benzyl)[5-(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyridin-2-yl]-amine

HRID 1367413Notes

Reaction equation

C1(S([N:10]2[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[C:12]([CH2:19][C:20]3[CH:21]=[CH:22][C:23]([NH:26][CH2:27][C:28]4[C:33]([F:34])=[CH:32][CH:31]=[CH:30][C:29]=4[Cl:35])=[N:24][CH:25]=3)=[CH:11]2)(=O)=O)C=CC=CC=1.CO.[OH-].[K+]>C(O)(=O)C>[Cl:35][C:29]1[CH:30]=[CH:31][CH:32]=[C:33]([F:34])[C:28]=1[CH2:27][NH:26][C:23]1[CH:22]=[CH:21][C:20]([CH2:19][C:12]2[C:13]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[NH:10][CH:11]=2)=[CH:25][N:24]=1

Participants

Conditions

Temperature: 80 °C

Procedure

[5-(1-Benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyridin-2-yl]-(2-chloro-6-fluoro-benzyl)-amine 617 was combined with methanol:potassium hydroxide (1M) (1:1, 0.5 mL). The mixture was heated at 80° C. for 2 hours. Acetic acid (0.1 mL) was added and the solvents removed under reduced pressure. The remaining residue was dissolved in dimethylsulfoxide (0.4 mL) and purified by reverse phase HPLC on a Phenomenex column (50 mm×10 mm ID) eluting with 0.1% trifluoroacetic acid in water and 20-100% acetonitrile wiith 0.1% trifluoroacetic acid over 16 minutes at a flow rate of 6 mL/minute to provide the desired compound P-0210. MS (ESI) [M+H+]+=367.1.

Workup

customthe solvents removed under reduced pressure
dissolutionThe remaining residue was dissolved in dimethylsulfoxide (0.4 mL)
custompurified by reverse phase HPLC on a Phenomenex column (50 mm×10 mm ID)
washeluting with 0.1% trifluoroacetic acid in water and 20-100% acetonitrile wiith 0.1% trifluoroacetic acid over 16 minutes at a flow rate of 6 mL/minute

Sources & evidence

ORD record: ord-4c85de2d36c54008ac893f41cc410c73
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07893075B2

Reaction notes

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