Dichloromethane → HCID 15950423, compound

HRID 507242Notes

Reaction equation

HRID 507242 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[F:13])[O:5][CH2:6][C:7](Cl)=[O:8].[S:14]1[CH:18]=[CH:17][N:16]=[C:15]1[NH:19][S:20]([C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[CH2:28][NH:27][CH2:26]2)(=[O:22])=[O:21].CCN(CC)CC.C(Cl)Cl>CC#N>[S:14]1[CH:18]=[CH:17][N:16]=[C:15]1[NH:19][S:20]([C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[CH2:28][N:27]([C:7](=[O:8])[CH2:6][O:5][C:4]1[CH:10]=[CH:11][C:12]([F:13])=[C:2]([Cl:1])[CH:3]=1)[CH2:26]2)(=[O:22])=[O:21]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 16495643(3-Chloro-4-fluorophenoxy)acetyl chlorideHCID 57542158HCID 57542158, compound

Product 1

HCID 15950423HCID 15950423, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-(3-Chloro-4-fluorophenoxy)acetyl chloride (52 mg, 0.23 mmol) was added to a stirring solution of 2,3-Dihydro-1H-isoindole-5-sulfonic acid thiazol-2-ylamide (65 mg, 0.23 mmol), Et3N (64 μl, 0.46 mmol) and CH2Cl2 (500 μl), under N2. The reaction mixture was stirred at room temperature for 30 minutes. Product formation was observed by LC/MS (10-99% CH3CN). Purification by Gilson preparative HPLC (10-99% CH3CN) gave the desired amide. LC/MS (10-99% CH3CN), M/Z: M+1 obs=468.1; tR=2.95 min.

Workup

  1. customPurification by Gilson preparative HPLC (10-99% CH3CN)

Sources & evidence

ORD record
ord-104ab76f603b418a9d4965f6ab02c2d3
Source dataset
uspto-grants-2010_08
Patent number
US07786137B2

Reaction notes

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