Ethanol → HCID 67494484, compound

HRID 2047229Notes

Reaction equation

HRID 2047229 reaction equation
[C:1]([BH3-])#[N:2].[Na+].[CH3:5][Si:6]([CH3:43])([CH3:42])[CH2:7][CH2:8][O:9][CH2:10][N:11]([CH2:34][O:35][CH2:36][CH2:37][Si:38]([CH3:41])([CH3:40])[CH3:39])[C:12]1[N:17]2[N:18]=[CH:19][C:20]([C:21]3[CH:22]=[N:23][C:24]4[C:29]([CH:30]=3)=[CH:28][C:27]([F:31])=[CH:26][CH:25]=4)=[C:16]2[N:15]=[C:14](C=O)[CH:13]=1.[CH3:44][NH2:45].[CH2:46](O)[CH3:47]>C(O)(=O)C>[CH2:44]([N:45]1[CH2:47][CH2:46][CH:14]([CH2:1][NH:2][C:14]2[CH:13]=[C:12]([N:11]([CH2:34][O:35][CH2:36][CH2:37][Si:38]([CH3:41])([CH3:39])[CH3:40])[CH2:10][O:9][CH2:8][CH2:7][Si:6]([CH3:5])([CH3:42])[CH3:43])[N:17]3[N:18]=[CH:19][C:20]([C:21]4[CH:22]=[N:23][C:24]5[C:29]([CH:30]=4)=[CH:28][C:27]([F:31])=[CH:26][CH:25]=5)=[C:16]3[N:15]=2)[CH2:13][CH2:12]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 6329MethylamineHCID 5003444Sodium cyanoborohydrideHCID 86664794HCID 86664794, compound

Product 1

HCID 67494484HCID 67494484, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Sodium cyanoborohydride (3.5 equiv) was added to a stirring mixture of aldehyde, 7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(6-fluoroquinolin-3-yl)pyrazolo[1,5-a]pyrimidine-5-carbaldehyde (1 equiv) and 1-benzylpiperidin-4-yl)methanamine (2 equiv) in ethanol and acetic acid at room temperature. When the reaction was deemed complete by HPLC, LC-MS, or TLC analysis, the mixture was quenched with saturated aqueous sodium bicarbonate, then extracted with dichloromethane (2×). The combined organics were dried over sodium sulfate, filtered, concentrated to dryness, and purified on silica gel to afford the desired product, N5-((1-benzylpiperidin-4-yl)methyl)-3-(6-fluoroquinolin-3-yl)-N7,N7-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidine-5,7-diamine.

Workup

  1. customthe mixture was quenched with saturated aqueous sodium bicarbonate
  2. extractionextracted with dichloromethane (2×)
  3. dry with materialThe combined organics were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. custompurified on silica gel

Sources & evidence

ORD record
ord-f9b4a98ed03a4d07a8100e06a47c76b3
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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