Acetic Acid → HCID 131730967, compound

HRID 2035504Notes

Reaction equation

HRID 2035504 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:30]=[C:31]([F:33])[CH:32]=1)[CH2:5][NH:6][C:7]1[CH:12]=[C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)=[CH:16][CH:15]=2)[N:10]=[CH:9][C:8]=1[CH2:26][C:27]([NH2:29])=[O:28].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[C:52]([NH:59][CH2:60][CH:61]=O)([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53]>C(Cl)(Cl)Cl>[C:55]([O:54][C:52]([NH:59][CH2:60][CH2:61][N:23]1[CH2:24][CH2:25][N:20]([C:17]2[CH:16]=[CH:15][C:14]([NH:13][C:11]3[N:10]=[CH:9][C:8]([CH2:26][C:27]([NH2:29])=[O:28])=[C:7]([NH:6][CH2:5][C:4]4[CH:3]=[C:2]([F:1])[CH:32]=[C:31]([F:33])[CH:30]=4)[CH:12]=3)=[CH:19][CH:18]=2)[CH2:21][CH2:22]1)=[O:53])([CH3:58])([CH3:57])[CH3:56]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 4247255tert-butyl N-(2-oxoethyl)carbamateHCID 5049666Sodium triacetoxyborohydrideHCID 131730963HCID 131730963, compound

Product 1

HCID 131730967HCID 131730967, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

20 mg of 4-[(3,5-difluorobenzyl)amino]-6-{[4-(piperazin-1-yl)phenyl]amino}pyridine-3-carboxyamide (the compound of Example 221) was dissolved in 0.5 mL of chloroform, to which 1.4 mg of acetic acid, 15 mg of sodium triacetoxyborohydride and 8.7 mg of N-Boc-2-aminoacetaldehyde were added, and stirred overnight at room temperature. The reaction mixture was washed with water and saturated saline, and dried on anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by silica gel thin layer chromatography (chloroform:methanol=5:1) to obtain 19 mg (71%) of the title compound as a light yellow solid.

Workup

  1. additionwere added
  2. washThe reaction mixture was washed with water and saturated saline
  3. dry with materialdried on anhydrous sodium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was purified by silica gel thin layer chromatography (chloroform:methanol=5:1)

Sources & evidence

ORD record
ord-307d5813b85a45ceb6ef32127d4e2df2
Source dataset
uspto-grants-2013_11
Patent number
US08575153B2

Reaction notes

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