Methylamine → HCID 59278130, compound

HRID 1698178Notes

Reaction equation

HRID 1698178 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3[CH:13]=[N:14][CH:15]=[C:16]([C:17]([NH:19][C@H:20]([C:23]4[CH:28]=[C:27]([S:29]([CH3:32])(=[O:31])=[O:30])[N:26]=[C:25](OS(C(F)(F)F)(=O)=O)[CH:24]=4)[CH2:21][CH3:22])=[O:18])[C:11]=3[CH:10]=[N:9]2)=[CH:4][CH:3]=1.CN.C1COCC1.C[CH2:49][N:50](C(C)C)C(C)C>CN(C=O)C.[Cl-].[NH4+]>[CH3:32][S:29]([C:27]1[CH:28]=[C:23]([C@@H:20]([NH:19][C:17]([C:16]2[C:11]3[CH:10]=[N:9][N:8]([C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)[C:12]=3[CH:13]=[N:14][CH:15]=2)=[O:18])[CH2:21][CH3:22])[CH:24]=[C:25]([NH:50][CH3:49])[N:26]=1)(=[O:30])=[O:31]

Participants

7

Reactant 4

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 59278225HCID 59278225, compound

Product 1

HCID 59278130HCID 59278130, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a stirred solution of trifluoromethanesulfonic acid 4-((S)-1-{[1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carbonyl]-amino}-propyl)-6-methanesulfonyl-pyridin-2-yl ester (0.08 g, 0.13 mmol) in DMF (2 mL) was added a 2.0 M solution of methylamine in THF (0.150 mL, 0.30 mmol) followed by DIPEA (0.05 mL, 0.3 mmol). After 16 hours, the mixture was diluted with saturated aqueous ammonium chloride (5 mL) and extracted with ethyl acetate (3×5 mL). The combined organic layers were dried over sodium sulfate and concentrated onto silica gel. The crude material was purified by silica gel chromatography eluting with a gradient of 0-100% ethyl acetate in hexanes to afford the title compound.

Workup

  1. extractionextracted with ethyl acetate (3×5 mL)
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. concentrationconcentrated onto silica gel
  4. customThe crude material was purified by silica gel chromatography
  5. washeluting with a gradient of 0-100% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-bccdcf1842674361a9023e0115581a16
Source dataset
uspto-grants-2012_04
Patent number
US08163918B2

Reaction notes

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