Tetramethylammonium Triacetoxyborohydride (>90%) → 4-phenoxy-N-((1-((2-(pyridin-2-yl)thiazol-5-yl)methyl)piperidin-4-yl)methyl)-1H-pyrazolo[4,3-c]pyridin-3-amine

HRID 2407830Notes

Reaction equation

HRID 2407830 reaction equation
FC(F)(F)C(O)=O.FC(F)(F)C(O)=O.[O:15]([C:22]1[C:27]2[C:28]([NH:31][CH2:32][CH:33]3[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]3)=[N:29][NH:30][C:26]=2[CH:25]=[CH:24][N:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl.Cl.Cl.[N:42]1[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=1[C:48]1[S:49][C:50]([CH2:53]N2CCC(CN)CC2)=[CH:51][N:52]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.C[N+](C)(C)C>C(#N)C>[O:15]([C:22]1[C:27]2[C:28]([NH:31][CH2:32][CH:33]3[CH2:38][CH2:37][N:36]([CH2:53][C:50]4[S:49][C:48]([C:43]5[CH:44]=[CH:45][CH:46]=[CH:47][N:42]=5)=[N:52][CH:51]=4)[CH2:35][CH2:34]3)=[N:29][NH:30][C:26]=2[CH:25]=[CH:24][N:23]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 13696215Tetramethylammonium Triacetoxyborohydride (>90%)HCID 66989375(1-((2-(Pyridin-2-yl)thiazol-5-yl)methyl)piperidin-4-yl)methanamine TrihydrochlorideHCID 866590634-phenoxy-N-(piperidin-4-ylmethyl)-1H-pyrazolo[4,3-c]pyridin-3-amine bis(2,2,2-trifluoroacetate)

Product 1

HCID 585040714-phenoxy-N-((1-((2-(pyridin-2-yl)thiazol-5-yl)methyl)piperidin-4-yl)methyl)-1H-pyrazolo[4,3-c]pyridin-3-amineYield 16.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of the compound prepared in Example 436 (0.053 g) and the compound prepared in Example 214 (0.039 g) in acetonitrile (1 mL) was stirred at room temperature for 30 minutes. Tetramethylammoniumtriacetoxy borohydride (0.094 g) was added and stirring at room temperature continued for 1 hour. The reaction mixture was quenched with aqueous saturated sodium bicarbonate. After stirring at room temperature for 20 minutes, hopeful product was extracted with ethyl acetate, washed with aqueous saturated sodium bicarbonate, dried, evaporated in vacuo to an oil that was purified by column chromatography on silica gel (1-5% methanol in dichloromethane) to provide the title compound (0.008 g) with the following physical data.

Workup

  1. customThe reaction mixture was quenched with aqueous saturated sodium bicarbonate
  2. stirringAfter stirring at room temperature for 20 minutes
  3. extractionhopeful product was extracted with ethyl acetate
  4. washwashed with aqueous saturated sodium bicarbonate
  5. customdried
  6. customevaporated in vacuo to an oil that
  7. customwas purified by column chromatography on silica gel (1-5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-1a4c0554acf4467385b8e03d6c928bf5
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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