Benzenemethanethiol, alpha,alpha-diphenyl- → HCID 67125572, compound

HRID 1184928Notes

Reaction equation

HRID 1184928 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:6]=[C:7]([NH:12][C:13](=[O:25])[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([C:23]#[N:24])([CH3:22])[CH3:21])[CH:15]=2)[CH:8]=[CH:9][C:10]=1[CH3:11])=[O:4].CCN(C(C)C)C(C)C.[C:35]1([C:41]([SH:54])([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>CN(C=O)C>[C:23]([C:20]([C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=1)[C:13]([NH:12][C:7]1[CH:8]=[CH:9][C:10]([CH3:11])=[C:5]([C:3](=[O:4])[CH2:2][S:54][C:41]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)([C:48]2[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=2)[C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[CH:6]=1)=[O:25])([CH3:22])[CH3:21])#[N:24]

Participants

5

Reactant 3

HCID 77281Benzenemethanethiol, alpha,alpha-diphenyl-HCID 81531DiisopropylethylamineHCID 86680182HCID 86680182, compound

Product 1

HCID 67125572HCID 67125572, compoundYield 70.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-(3-(2-bromoacetyl)-4-methylphenyl)-3-(2-cyanopropan-2-yl)benzamide 113 (1.127 mmol, 450 mg), DIPEA (1.352 mmol, 0.224 mL) and triphenylmethyl mercaptan (1.240 mmol, 343 mg) in DMF (5 ml) was stirred overnight at room temperature. Evaporated to dryness. Purification by chromatography (0-10% ethyl acetate in Toluene) gave 3-(2-cyanopropan-2-yl)-N-(4-methyl-3-(2-(tritylthio)acetyl)phenyl)benzamide 114 (475 mg, 70.9%). NMR (400 MHz, CDCl3) 1.80 (s, 6H), 2.38 (s, 3H), 3.55 (s, 2H), 7.31-7.15 (m, 10H), 7.39 (d, J=2.3 Hz, 1H), 7.42 (m, 3H), 7.44 (m, 3H), 7.56 (t, J=7.8 Hz, 1H), 7.72 (m, 2H), 7.74 (m, 1H), 7.79 (d, J=7.8 Hz, 1H), 7.99 (t, J=1.9 Hz, 1H).

Workup

  1. customEvaporated to dryness
  2. customPurification by chromatography (0-10% ethyl acetate in Toluene)

Sources & evidence

ORD record
ord-a3d29145f28f4020a994202672157785
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

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