Sodium borohydride → N-(3-(6-(4-(1,4-Dimethyl-3-oxopiperazin-2-yl)phenylamino)-4-methyl-5-oxo-4,5-dihydropyrazin-2-yl)-2-methylphenyl)-7-hydroxy-4,5,6,7-tetrahydrobenzo[b]thiophene-2-carboxamide

HRID 1363496Notes

Reaction equation

HRID 1363496 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH3:8])[C:4](=[O:9])[CH:3]1[C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]2[C:18](=[O:44])[N:19]([CH3:43])[CH:20]=[C:21]([C:23]3[C:24]([CH3:42])=[C:25]([NH:29][C:30]([C:32]4[S:36][C:35]5[C:37](=[O:41])[CH2:38][CH2:39][CH2:40][C:34]=5[CH:33]=4)=[O:31])[CH:26]=[CH:27][CH:28]=3)[N:22]=2)=[CH:12][CH:11]=1.[BH4-].[Na+]>CO>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH3:8])[C:4](=[O:9])[CH:3]1[C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]2[C:18](=[O:44])[N:19]([CH3:43])[CH:20]=[C:21]([C:23]3[C:24]([CH3:42])=[C:25]([NH:29][C:30]([C:32]4[S:36][C:35]5[CH:37]([OH:41])[CH2:38][CH2:39][CH2:40][C:34]=5[CH:33]=4)=[O:31])[CH:26]=[CH:27][CH:28]=3)[N:22]=2)=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 25234214N-(3-(6-(4-(1,4-Dimethyl-3-oxopiperazin-2-yl)phenylamino)-4-methyl-5-oxo-4,5-dihydropyrazin-2-yl)-2-methylphenyl)-7-oxo-4,5,6,7-tetrahydrobenzo[b]thiophene-2-carboxamide

Product 1

HCID 57625123N-(3-(6-(4-(1,4-Dimethyl-3-oxopiperazin-2-yl)phenylamino)-4-methyl-5-oxo-4,5-dihydropyrazin-2-yl)-2-methylphenyl)-7-hydroxy-4,5,6,7-tetrahydrobenzo[b]thiophene-2-carboxamideYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A 50-mL single-neck round-bottomed flask equipped with a magnetic stirrer was purged with nitrogen and charged with 17 (250 mg, 0.409 mmol) and methanol (10 mL). The resulting solution was cooled to 0° C., and sodium borohydride (31 mg, 0.819 mmol) was added. After stirring the reaction at room temperature for 2 h, the solvent was evaporated under reduced pressure. The resulting residue was purified by flash chromatography to afford 18 in 88% yield (220 mg) as a white solid: mp 165-166° C.; 1H NMR (500 MHz, CD2Cl2) δ 8.38 (s, 1H), 7.90 (d, 1H, J=7.5 Hz), 7.81 (d, 2H, J=8.5 Hz), 7.71 (s, 1H), 7.39 (s, 1H), 7.34-7.27 (m, 4H), 6.80 (s, 1H), 4.94 (m, 1H), 3.72 (td, 1H, J=11.5, 4.5 Hz), 3.65 (s, 1H), 3.62 (s, 3H), 3.21 (m, 1H), 3.01 (m, 1H), 2.95 (s, 3H), 2.76-2.62 (m, 3H), 2.43 (s, 3H), 2.22-2.13 (m, 5H), 2.02 (m, 1H), 1.83 (m, 2H); MS (ESI+) m/z 595.2 (M+H).

Workup

  1. customA 50-mL single-neck round-bottomed flask equipped with a magnetic stirrer
  2. customwas purged with nitrogen
  3. customthe reaction at room temperature for 2 h
  4. customthe solvent was evaporated under reduced pressure
  5. customThe resulting residue was purified by flash chromatography

Sources & evidence

ORD record
ord-78a21bdbcac34432b8cf18cd94b0d27a
Source dataset
uspto-grants-2011_02
Patent number
US07884108B2

Reaction notes

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