Methanol → HCID 68182892, compound

HRID 1615578Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][NH:12][C:11](=[O:14])[C:10]3[S:15][C:16]([N:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)=[C:17]([CH:18]=[O:19])[C:9]2=3)=[CH:4][CH:3]=1.CO.[BH4-].[Na+]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][NH:12][C:11](=[O:14])[C:10]3[S:15][C:16]([N:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)=[C:17]([CH2:18][OH:19])[C:9]2=3)=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 887Methanol

HCID 4311764Sodium borohydride

HCID 86669801HCID 86669801, compound

Product 1

HCID 68182892HCID 68182892, compoundYield 62.7%

Procedure

To a solution of 4-(4-chlorophenyl)-2-(morpholin-4-yl)-7-oxo-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carbaldehyde (52.4 mg, 0.139 mmol, single enantiomer of unknown configurate) in methanol (1.30 mL, 32.0 mmol) was added portionwise sodium borohydride (10.5 mg, 0.278 mmol). The reaction mixture was stirred at rt for 1.5 hr, then carefully quenched by the addition of an aqueous solution of 1M HCl to lower the pH to ˜3-4. The mixture was extracted w/EA twice, the extracts were combined, washed w/brine, dried over Na2SO4, filtered, and concentrated in vacuo. HPLC purification provided the title compound as a white solid (33 mg, 62%). LCMS: (FA) ES+ 379, 381. 1H NMR (400 MHz, DMSO) δ 7.41 (d, J=4.4 Hz, 1H), 7.38-7.33 (m, 2H), 7.03-7.01 (m, 2H), 4.97 (t, J=4.9 Hz, 1H), 4.36 (d, J=4.5 Hz, 1H), 4.19 (dd, J=11.9, 5.4 Hz, 1H), 3.91-3.82 (m, 2H), 3.78-3.66 (m, 4H), 3.31-3.25 (m, 1H), 3.20-3.12 (m, 2H), 3.00-2.92 (m, 2H).

Workup

customcarefully quenched by the addition of an aqueous solution of 1M HCl
extractionThe mixture was extracted w/EA twice
washwashed w/brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customHPLC purification

Sources & evidence

ORD record: ord-72d78a364184442f923fefb81e2c7e64
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765746B2

Reaction notes

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