Sodium borohydride → HCID 117739222, compound

HRID 1507143Notes

Reaction equation

[CH2:1]([N:8]([CH3:31])[CH2:9][CH2:10][CH2:11][N:12]([CH2:19][C:20]1[CH:25]=[C:24]([C:26](OCC)=[O:27])[CH:23]=[CH:22][N:21]=1)C(=O)C(F)(F)F)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>>[CH2:1]([N:8]([CH3:31])[CH2:9][CH2:10][CH2:11][NH:12][CH2:19][C:20]1[CH:25]=[C:24]([CH2:26][OH:27])[CH:23]=[CH:22][N:21]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 4311764Sodium borohydride

HCID 90375093HCID 90375093, compound

Product 1

HCID 117739222HCID 117739222, compound

Procedure

By General Procedure U from ethyl 2-[(N-{3-[benzyl(methyl)amino]propyl}-2,2,2-trifluoroacetamido)methyl]pyridine-4-carboxylate using 5.0 equiv. of NaBH4. Purification by column chromatography gave the title product. 1H NMR (300 MHz, CDCl3) 8 ppm: 8.5 (dd, 1H), 7.80 (s, 1H), 7.6-7.3 (m, 1H), 4.6 (s, 2H), 4.3 (s, 2H), 3.6-3.2 (m, 4H), 2.8 (s, 3H), 2.2-2.0 (m, 2H), 1.7-1.3 (m, 3H).

Workup

customPurification by column chromatography

Sources & evidence

ORD record: ord-98ea1e28a12d4475acd3975acf92741f
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221801B2

Reaction notes

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