Sodium borohydride → HCID 90374872, compound

HRID 1507158Notes

Reaction equation

[CH2:1]([N:3]([CH2:31][CH3:32])[CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:9]([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)=[O:10])[CH3:2].[BH4-].[Na+]>>[CH2:31]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:9](=[O: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)[CH3:32]

Participants

Reactant 2

HCID 4311764Sodium borohydride

HCID 90375180HCID 90375180, compound

Product 1

HCID 90374872HCID 90374872, compound

Procedure

Prepared by General Procedure U from ethyl 2-{[N-({[4-(diethylamino)butyl]carbamoyl}methyl)-2,2,2-trifluoroacetamido]methyl}pyridine-4-carboxylate, using 5 equivalents of NaBH4. Purification by column chromatography with (10% MeOH and 1% NH4OH in DCM) gave the title product as light yellow oil. 1H NMR (300 MHz, methanol-d4): δ ppm 8.45 (d, 1H), 7.47 (s, 1H), 7.31 (d, 1H), 4.68 (s, 2H), 3.88 (s, 2H), 3.28 (m, 4H), 2.59 (q, 4H), 2.51 (m, 2H), 1.52 (m, 4H), 1.05 (t, 6H).

Workup

customPurification by column chromatography with (10% MeOH and 1% NH4OH in DCM)

Sources & evidence

ORD record: ord-7f7ae79cb4d949fd8027c1080548a8a1
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221801B2

Reaction notes

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