Sodium borohydride → 5-(3-(2-hydroxy-2-phenylethyl)-2-oxoimidazolidin-1-yl)-3-methyl-N-(pyridin-3-ylmethyl)thiophene-2-carboxamide

HRID 560912Notes

Reaction equation

HRID 560912 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([N:7]2[CH2:11][CH2:10][N:9]([CH2:12][C:13](=[O:20])[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:8]2=[O:21])[S:4][C:3]=1[C:22]([NH:24][CH2:25][C:26]1[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=1)=[O:23].[BH4-].[Na+]>CO.C(Cl)(Cl)Cl>[OH:20][CH:13]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH2:12][N:9]1[CH2:10][CH2:11][N:7]([C:5]2[S:4][C:3]([C:22]([NH:24][CH2:25][C:26]3[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=3)=[O:23])=[C:2]([CH3:1])[CH:6]=2)[C:8]1=[O:21]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 594811793-methyl-5-(2-oxo-3-(2-oxo-2-phenylethyl)imidazolidin-1-yl)-N-(pyridin-3-ylmethyl)thiophene-2-carboxamide

Product 1

HCID 594812685-(3-(2-hydroxy-2-phenylethyl)-2-oxoimidazolidin-1-yl)-3-methyl-N-(pyridin-3-ylmethyl)thiophene-2-carboxamideYield 92%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 3-methyl-5-(2-oxo-3-(2-oxo-2-phenylethyl)imidazolidin-1-yl)-N-(pyridin-3-ylmethyl)thiophene-2-carboxamide (0.09 g, 0.20 mmol) in methanol (3 mL) and chloroform (1.5 mL) at 0° C. was added sodium borohydride (0.01 g, 0.29 mmol) under nitrogen atmosphere. The resulting mixture was stirred at 0° C. for 1 h, and then quenched with water (25 mL). The aqueous layer was extracted with dichloromethane (2×50 mL), and the combined organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was triturated with dichloromethane in hexanes to afford the title compound as a brownish solid in 92% yield (0.08 g): mp 75° C. (dec.); 1H NMR (300 MHz, CDCl3) δ 8.52 (s, 1H), 8.43 (s, 1H), 7.65 (d, J=7.8 Hz, 1H), 7.39-7.17 (m, 6H), 6.37 (t, J=5.5 Hz, 1H), 5.98 (s, 1H), 4.94 (dd, J=7.7, 3.3 Hz, 1H), 4.52 (d, J=5.5 Hz, 2H), 3.87 (br s, 1H), 3.75-3.35 (m, 6H), 2.43 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 163.6, 156.6, 149.0, 148.5, 142.4, 141.7, 141.6, 135.6, 134.3, 128.5, 127.9, 125.8, 123.6, 119.0, 112.4, 72.8, 52.3, 43.8, 43.1, 41.1, 16.1; MS (ES+) m/z 437.4 (M+1).

Workup

  1. customquenched with water (25 mL)
  2. extractionThe aqueous layer was extracted with dichloromethane (2×50 mL)
  3. dry with materialthe combined organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated with dichloromethane in hexanes

Sources & evidence

ORD record
ord-cb649a6a0edd47f8ad93435ecc665859
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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