Glutaraldehyde → HCID 11649596, compound

HRID 2056703Notes

Reaction equation

HRID 2056703 reaction equation
[NH2:1][C:2]([CH3:33])([CH3:32])[CH2:3][NH:4][C:5]1[N:10]=[C:9]([O:11][C:12]2[C:17]3[N:18]=[C:19]([NH2:21])[S:20][C:16]=3[CH:15]=[CH:14][CH:13]=2)[CH:8]=[C:7]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=2)[N:6]=1.[CH2:34]([CH2:38][CH:39]=O)[CH2:35][CH:36]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH3:32][C:2]([N:1]1[CH2:39][CH2:38][CH2:34][CH2:35][CH2:36]1)([CH3:33])[CH2:3][NH:4][C:5]1[N:10]=[C:9]([O:11][C:12]2[C:17]3[N:18]=[C:19]([NH2:21])[S:20][C:16]=3[CH:15]=[CH:14][CH:13]=2)[CH:8]=[C:7]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:29])([F:30])[F:31])=[CH:24][CH:23]=2)[N:6]=1

Participants

5

Reactant 3

HCID 3485GlutaraldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 58612004HCID 58612004, compound

Product 1

HCID 11649596HCID 11649596, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a mixture of 4-(2-(2-amino-2-methylpropylamino)-6-(4-(trifluoromethyl)phenyl)pyrimidin-4-yloxy)benzo[d]thiazol-2-amine (47 mg, 1.0 mmol, Example 80) and 50% aqueous solution of glutaric dialdehyde (40 mg, 0.2 mmol, Aldrich) in 1,2-dichloroethane (2 mL) was added sodium triacetoxyborohydride (212 mg, 1.0 mmol, Aldrich) and the mixture was stirred at room temperature for 1 h. The reaction mixture was evaporated under reduced pressure and the residue was treated with sat. aqueous solution of NaHCO3 (5 mL), and extracted with EtOAc (2×20 mL). The combined EtOAc extracts were washed with brine, dried over Na2SO4 and filtered. The filtrate was evaporated in vacuo and the residue was purified by silica gel column chromatography (10% MeOH/DCM) to afford the title compound as a white amorphous solid. MS (ESI, pos. ion.) m/z: 543 (M+1).

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. additionthe residue was treated with sat. aqueous solution of NaHCO3 (5 mL)
  3. extractionextracted with EtOAc (2×20 mL)
  4. washThe combined EtOAc extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customThe filtrate was evaporated in vacuo
  8. customthe residue was purified by silica gel column chromatography (10% MeOH/DCM)

Sources & evidence

ORD record
ord-0673eb6e03eb4e43a69a88f28ff2b2ff
Source dataset
uspto-grants-2008_02
Patent number
US07335672B2

Reaction notes

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