Sodium borohydride → HCID 90375064, compound

HRID 1507147Notes

Reaction equation

FC(F)(F)C([N:5]([CH2:25][C:26]1[CH:31]=[C:30]([C:32](OCC)=[O:33])[CH:29]=[CH:28][N:27]=1)[CH2:6][C:7](=[O:24])[NH:8][CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22][CH3:23])[CH2:11][CH2:10]1)=O.[BH4-].[Na+]>>[OH:33][CH2:32][C:30]1[CH:29]=[CH:28][N:27]=[C:26]([CH2:25][NH:5][CH2:6][C:7]([NH:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[O:22][CH3:23])[CH2:11][CH2:10]2)=[O:24])[CH:31]=1

Participants

Reactant 2

HCID 4311764Sodium borohydride

HCID 90094314HCID 90094314, compound

Product 1

HCID 90375064HCID 90375064, compound

Procedure

By General Procedure U from ethyl 2-({2,2,2-trifluoro-N-[({1-[(2-methoxyphenyl)methyl]piperidin-4-yl}carbamoyl)methyl]acetamido}methyl)pyridine-4-carboxylate using 5 equiv. of NaBH4. Purification by column chromatography using 1% MeOH/DCM to 28% MeOH/DCM/1% NH4OH as elutent to get the product as an off white solid. 1H-NMR (300 MHz, CDCl3): δ 8.42 (d, 1H), 7.42 (d, 1H), 7.35 (d, 1H), 7.25 (m, 2H), 7.15 (m, 1H), 6.99-6.85 (m, 2H), 4.65 (s, 2H), 3.80 (m, 4H), 3.60 (s, 2H), 3.45 (s, 2H), 3.25 (s, 2H), 2.90 (m, 2H), 2.22 (m, 2H), 1.90 (m, 2H), 1.60 (m, 2H).

Workup

customPurification by column chromatography
customto get the product as an off white solid

Sources & evidence

ORD record: ord-a54b65db3e094471af22b741fdfbc143
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221801B2

Reaction notes

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