Sodium triacetoxyborohydride → HCID 178521405, compound

HRID 1399806Notes

Reaction equation

[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]1[CH2:11][CH:12]([OH:23])[CH2:13][O:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=O.[NH:24]1[CH:28]=[CH:27][C:26]([NH2:29])=[N:25]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[NH:24]1[CH:28]=[CH:27][C:26]([NH:29][CH2:18][C:17]2[CH:16]=[C:15]([CH:22]=[CH:21][CH:20]=2)[O:14][CH2:13][CH:12]([OH:23])[CH2:11][N:2]2[CH2:3][CH2:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH2:1]2)=[N:25]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 3-(3-(3,4-dihydroisoquinolin-2(1H)-yl)-2-hydroxypropoxy)benzaldehyde (200 mg, 0.64 mmol) in DCM (15 mL) was added 1H-pyrazol-3-amine (80 mg, 0.96 mmol). The solution was heated at 60° C. for 0.5 h. NaBH(OAc)3 (204 mg, 0.96 mmol) was then added into the reaction mixture which was heated at 60° C. for another 1 h. The reaction mixture was quenched by adding 1N HCl aqueous solution and diluted with DCM and washed with NaHCO3 aqueous solution. The separated organic layer was concentrated and the crude product was purified by preparative HPLC purification. (26 mg, yield 11%). MS (ESI+) e/z: 379.1 [M+1]+. 1H NMR (MeOD, 400 MHz), δ ppm: 7.33-7.18 (m, 7H), 7.00-6.96 (m, 2H), 6.84-6.80 (m, 1H), 4.48-4.44 (m, 3H), 4.28 (s, 1H), 4.06-3.98 (m, 2H), 3.59-3.56 (m, 2H), 3.42-3.39 (m, 2H), 3.20-3.15 (m, 2H).

Workup

temperaturewas heated at 60° C. for another 1 h
customThe reaction mixture was quenched
additionby adding 1N HCl aqueous solution
additiondiluted with DCM
washwashed with NaHCO3 aqueous solution
concentrationThe separated organic layer was concentrated
customthe crude product was purified by preparative HPLC purification

Sources & evidence

ORD record: ord-5aea526bab8d4f2ca810c99492666461
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906900B2

Reaction notes

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