Formaldehyde → HCID 71730896, compound

HRID 2206324Notes

Reaction equation

HRID 2206324 reaction equation
Cl.[Cl:2][C:3]1[C:8]2[N:9]=[C:10]([C:12]3[C:27](=[O:28])[O:26][C:15]4=[N:16][C:17]([N:20]5[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]5)=[CH:18][CH:19]=[C:14]4[CH:13]=3)[S:11][C:7]=2[CH:6]=[CH:5][CH:4]=1.[CH3:29]N(C=O)C.C=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>O>[Cl:2][C:3]1[C:8]2[N:9]=[C:10]([C:12]3[C:27](=[O:28])[O:26][C:15]4=[N:16][C:17]([N:20]5[CH2:25][CH2:24][N:23]([CH3:29])[CH2:22][CH2:21]5)=[CH:18][CH:19]=[C:14]4[CH:13]=3)[S:11][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 6228DimethylformamideHCID 5049666Sodium triacetoxyborohydrideHCID 89781818HCID 89781818, compound

Product 1

HCID 71730896HCID 71730896, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 3-(4-chlorobenzo[d]thiazol-2-yl)-7-(piperazin-1-yl)-2H-pyrano[2,3-b]pyridin-2-one hydrochloride (890 mg, 2.0 mmol) m DMF (10 mL) were added 37% aqueous HCHO (0.4 mL, 3.4 mmol) and then NaBH(OAc)3 (636 mg, 3.0 mmol). The reaction mixture was stirred for 30 min at ambient temperature. To the mixture were added water (10 mL) and a saturated NaHCO3 solution (10 mL) to form a precipitate. The precipitate was filtered off, washed with water and dried under nitrogen, affording 680 mg (97%) of the title compound as a yellow solid. Melting point 258-260° C.; MS m/z 413.2 [M+H]+; 1H NMR (500 MHz, DMSO-d6) δ (ppm) 9.06 (1H, s), 8.25 (1H, d, J=8.8 Hz), 8.14 (1H, d, J=6.9 Hz), 7.64 (1H, m), 7.44 (1H, d, J=7.7 Hz), 7.08 (1H, d, J=9.1 Hz), 3.79 (4H, m), 2.44 (4H, m), 2.25 (3H, s).

Sources & evidence

ORD record
ord-f26c632d53ee4259bbe1ab6d6add515f
Source dataset
uspto-grants-2016_06
Patent number
US09371336B2

Reaction notes

Loading…