6-Amino-2-(2-pyrrolidin-1-yl-ethylamino)benzothiazole → N-[2-(2-pyrrolidin-1-ylethylamino)-benzothiazol-6-yl]-2-thiophenecarboximidamide

HRID 723949Notes

Reaction equation

HRID 723949 reaction equation
[NH2:1][C:2]1[CH:18]=[CH:17][C:5]2[N:6]=[C:7]([NH:9][CH2:10][CH2:11][N:12]3[CH2:16][CH2:15][CH2:14][CH2:13]3)[S:8][C:4]=2[CH:3]=1.Br.C1(S[C:27]([C:29]2[S:30][CH:31]=[CH:32][CH:33]=2)=[NH:28])C=CC=CC=1>C(O)C>[N:12]1([CH2:11][CH2:10][NH:9][C:7]2[S:8][C:4]3[CH:3]=[C:2]([NH:1][C:27]([C:29]4[S:30][CH:31]=[CH:32][CH:33]=4)=[NH:28])[CH:18]=[CH:17][C:5]=3[N:6]=2)[CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 218784956-Amino-2-(2-pyrrolidin-1-yl-ethylamino)benzothiazoleHCID 66912440Thiophene-2-carboximidothioic acid phenyl ester hydrobromide

Product 1

HCID 178511932N-[2-(2-pyrrolidin-1-ylethylamino)-benzothiazol-6-yl]-2-thiophenecarboximidamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-Amino-2-(2-pyrrolidin-1-yl-ethylamino)benzothiazole (Example 12, 28 mg, 0.11 mmol) and thiophene-2-carboximidothioic acid phenyl ester hydrobromide (32 mg, 0.11 mmol) in 3 mL of ethanol (denatured) was stirred at room temperature for 20 hours. The solvent was removed and the residue was partitioned between 5 mL of H2O and 10 mL of Et2O. The aqueous layer was concentrated to give the title compound. 1H-NMR (CD3OD): δ 8.08 (m, 2H); 7.72 (d, 1H, J=2.0 Hz); 7.64 (d, 1H, J=8.0 Hz); 7.30 (m, 2H); 3.86 (t, 2H, J=5.9 Hz); 3.50 (m, 6H); 2.10 (m, 4H).

Workup

  1. customThe solvent was removed
  2. customthe residue was partitioned between 5 mL of H2O and 10 mL of Et2O
  3. concentrationThe aqueous layer was concentrated

Sources & evidence

ORD record
ord-df6cd12d57db4dc388456ceed0542343
Source dataset
uspto-grants-2006_11
Patent number
US07141595B2

Reaction notes

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