Acetic Acid → HCID 57979900, compound

HRID 1867750Notes

Reaction equation

HRID 1867750 reaction equation
[Cl:1][C:2]1[C:3]([F:30])=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:28][CH3:29])=[C:16]([CH2:19][NH:20][C@H:21]4[CH2:26][CH2:25][CH2:24][NH:23][C:22]4=[O:27])[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.[C:31](O)(=O)C.C([O-])(=O)C.[Na+].C([BH3-])#N.[Na+]>C=O>[Cl:1][C:2]1[C:3]([F:30])=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:28][CH3:29])=[C:16]([CH2:19][N:20]([CH3:31])[C@H:21]4[CH2:26][CH2:25][CH2:24][NH:23][C:22]4=[O:27])[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 57979833HCID 57979833, compound

Product 1

HCID 57979900HCID 57979900, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 712FormaldehydeSolvent

Conditions

Temperature
-10 °C

Procedure

(3S)-3-[({4-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)amino]piperidin-2-one (165 mg, 0.38 mmol, Example 85) was dissolved in 37% aqueous formaldehyde (2 ml) and acetic acid (0.22 ml, 3.84 mmol) and sodium acetate (315 mg, 3.84 mmol) added. The mixture was cooled to −10° C. and sodium cyanoborohydride (24 mg, 0.38 mmol) added. The mixture was stirred for 15 minutes and then purified by reverse phase HPLC to give the title product (114 mg, 67%) as a white solid; 1H NMR Spectrum: (DMSO d6) 1.77 (m, 3H); 2.02 (m, 1H); 2.40 (s, 3H); 3.09 (m, 2H); 3.29 (dd, 1H); 3.95 (s, 5H); 7.18 (s, 1H); 7.28 (t, 1H); 7.40 (brs, 1H); 7.48 (t, 1H); 7.55 (m, 1H); 8.35 (s, 1H); 8.42 (s, 1H); 9.76 (s, 1H). Mass Spectrum: (M+H)+ 444.

Workup

  1. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-5d57cd147cfe4b8e814999f65d22d107
Source dataset
uspto-grants-2009_12
Patent number
US07632840B2

Reaction notes

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