1-Hydroxybenzotriazole → N-(2-Phenylsulfonyl-1-ethyl) 3-(4-Cyanophenyl)-2,3-dihydro-imidazo[2,1-b]thiazole-5-carboxamide hydrochloride

HRID 844261Notes

Reaction equation

HRID 844261 reaction equation
[ClH:1].[C:2]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:14][S:13][C:12]3=[N:15][CH:16]=[C:17]([C:18]([OH:20])=O)[N:11]23)=[CH:6][CH:5]=1)#[N:3].Cl.[C:22]1([S:28]([CH2:31][CH2:32][NH2:33])(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)C(C)C)(C)C>>[ClH:1].[C:22]1([S:28]([CH2:31][CH2:32][NH:33][C:18]([C:17]2[N:11]3[C:12]([S:13][CH2:14][CH:10]3[C:7]3[CH:6]=[CH:5][C:4]([C:2]#[N:3])=[CH:9][CH:8]=3)=[N:15][CH:16]=2)=[O:20])(=[O:29])=[O:30])[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 136550652-(Phenylsulfonyl)ethanamine hydrochlorideHCID 699341033-(4-Cyanophenyl)-2,3-dihydro-imidazo[2,1-b]thiazole-5-carboxylic acid hydrochloride

Product 1

HCID 70119480N-(2-Phenylsulfonyl-1-ethyl) 3-(4-Cyanophenyl)-2,3-dihydro-imidazo[2,1-b]thiazole-5-carboxamide hydrochloride

Procedure

The carboxylic acid from Step D (60.0 mg, 0.188 mmol), amine from Step G (41.6 mg, 0.188 mmol), EDC hydrochloride (43.2 mg, 0.225 mmol), HOBT (30.4 mg, 0.225 mmol), and N,N-diisopropylethylamine (0.163 mL, 0.938 mmol) were stirred in dry, degassed DMF (1 mL) at 25° C. for 16 hours. The crude product was purified by preparative HPLC using a gradient of 5%-95% acetonitrile/0.1% TFA; 95%-5%/0.1% aqueous TFA over 15 min. The title compound was isolated after conversion to the HCl salt. MS (es) m+1=439. 1H-NMR (CD3OD): δ7.87 (d, 2H, J=7.8 Hz); 7.71 (d, 2H, J=8.5 Hz); 7.70 (t, 1H, J=7.8 Hz); 7.59 (t, 2H, J=7.7 Hz); 7.49 (s, 1H); 7.17 (d, 2H, J=8.0 Hz); 6.24 (bd, 1H, J=7.7 Hz); 4.64 (dd, 1H, J=12.3, 8.9 Hz); 3.74 (d, 1H, J=12.3 Hz), 3.28-3.57 (m, 4H).

Workup

  1. customin dry
  2. customdegassed DMF (1 mL) at 25° C. for 16 hours
  3. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-4b1865e9043e442998722879fd216a69
Source dataset
uspto-grants-2002_04
Patent number
US06380228B1

Reaction notes

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