Sodium triacetoxyborohydride → HCID 90015286, compound

HRID 1057049Notes

Reaction equation

Cl.[CH3:2][C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]1[N:13]=[C:12]([NH:14][C:15]2[CH:20]=[C:19]([C:21]#[N:22])[CH:18]=[CH:17][N:16]=2)[CH:11]=[C:10]([CH:23]2[CH2:27][CH2:26][NH:25][CH2:24]2)[CH:9]=1.[O:28]1[CH2:33][CH2:32][CH:31]([CH:34]=O)[CH2:30][CH2:29]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[CH3:2][C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]1[N:13]=[C:12]([NH:14][C:15]2[CH:20]=[C:19]([CH:18]=[CH:17][N:16]=2)[C:21]#[N:22])[CH:11]=[C:10]([CH:23]2[CH2:27][CH2:26][N:25]([CH2:34][CH:31]3[CH2:32][CH2:33][O:28][CH2:29][CH2:30]3)[CH2:24]2)[CH:9]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 2-[[6-[(2R)-2-methylpyrrolidin-1-yl]-4-pyrrolidin-3-yl-2-pyridyl]amino]pyridine-4-carbonitrile hydrochloride (160 mg, 0.415 mmol) in methanol (3.0 mL) was added tetrahydropyran-4-carbaldehyde (0.086 mL, 0.831 mmol, 2.0 equiv.). It was heated @ 50° C. overnight. After cooling to room temperature, sodium triacetoxyborohydride (278.2 mg, 1.247 mmol, 3.0 equiv.) was added in portions. After 3 h, more sodium triacetoxyborohydride (278.2 mg, 1.247 mmol, 3.0 equiv.) was added, stirred @ rt for another o/n. It was quenched with 1N NaHCO3, extracted with EtOAc (2×20 mL), dried over Na2SO4, filtered, concentrated in vacuo, and purified by HPLC to afford 15.5 mg (8.3%) of product as yellow gum. LC-MS: m/z=447 (M+H+).

Workup

temperatureAfter cooling to room temperature
customIt was quenched with 1N NaHCO3
extractionextracted with EtOAc (2×20 mL)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
custompurified by HPLC

Sources & evidence

ORD record: ord-80551169aa0d4bd2b2d5a705f394768d
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09399636B2

Reaction notes

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