Chloroacetaldehyde → Ammonium Hydroxide

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A solution of (6S)-3-{3-[(8R)-8-(3,5-difluorophenyl)-8-methyl-10-oxo-6,9-diazaspiro[4.5]dec-9-yl]prop-1-yn-1-yl}-5,7-dihydrospiro[cyclopenta[b]pyridine-6,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one (100 mg, 0.18 mmol, described in Example 39), acetic acid (0.041 mL, 0.72 mmol), and chloroacetaldehyde (0.47 mL, 3.6 mmol, 50 wt % in H2O) in MeOH (5 mL) was stirred for 5 min. Sodium cyanoborohydride (34 mg, 0.54 mmol) was added and stirring was continued for 42 h. Additional chloroacetaldehyde (0.47 mL, 3.6 mmol, 50 wt % in H2O) and sodium cyanoborohydride (34 mg, 0.54 mmol) was added at 24 h. The reaction was quenched with saturated aqueous NaHCO3 (10 mL) and extracted with CH2Cl2 (3×10 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified on silica gel, eluting with a gradient of CH2Cl2:MeOH:NH4OH—100:0:0 to 90:10:1, to yield the title compound. MS: m/z=616 (M+1).

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