Dichloromethane → HCID 46846826, compound

HRID 330809Notes

Reaction equation

HRID 330809 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][N:6]1[C:10]2[CH:11]=[C:12]([Cl:15])[CH:13]=[CH:14][C:9]=2[S:8][C:7]1=[O:16].Cl[C:21]([OH:23])=[O:22].[CH3:24][N:25]1[CH2:30][CH2:29][N:28]([CH2:31][CH2:32][CH3:33])[CH2:27][CH2:26]1.CCN(C(C)C)C(C)C.ClCCl>C1COCC1>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]2[S:8][C:7](=[O:16])[N:6]([CH2:5][C:4]3[CH:3]=[C:2]([NH:1][C:21](=[O:22])[O:23][CH2:33][CH2:32][CH2:31][N:28]4[CH2:29][CH2:30][N:25]([CH3:24])[CH2:26][CH2:27]4)[CH:19]=[CH:18][CH:17]=3)[C:10]=2[CH:11]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 58496340HCID 58496340, compoundHCID 86658945HCID 86658945, compound

Product 1

HCID 46846826HCID 46846826, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

173 mg (0.36 mmol) of 3-(3-aminobenzyl)-5-chloro-3H-benzothiazol-2-one and 198 mg (0.67 mmol) of 3-(4-methylpiperazin-1-yl)propane 1-chloroformate are suspended in 3 ml of THF, and 253 μl (1.46 mmol) of DIPEA are added. The reaction mixture is stirred overnight at room temperature. 50 ml of dichloromethane are added to the suspension, which is subsequently washed with 10 ml of 2N NaOH, dried and evaporated. The crude product is purified by means of preparative HPLC. The product “A13” is in the form of the trifluoroacetate.

Workup

  1. washis subsequently washed with 10 ml of 2N NaOH
  2. customdried
  3. customevaporated
  4. customThe crude product is purified by means of preparative HPLC

Sources & evidence

ORD record
ord-d35f6516ad5c49a1a37ec5e77f19cdca
Source dataset
uspto-grants-2014_11
Patent number
US08877751B2

Reaction notes

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