Phenyl-2-aminoethyl sulfide → N-(2-Phenylthio-1-ethyl) 3-(4-Cyanophenyl)-2,3-dihydro-imidazo[2,1-b]thiazole-5-carboxamide hydrochloride

HRID 844262Notes

Reaction equation

HRID 844262 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].[C:21]1([S:27][CH2:28][CH2:29][NH2:30])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=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:21]1([S:27][CH2:28][CH2:29][NH:30][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])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 5

HCID 37013Phenyl-2-aminoethyl sulfideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 699341033-(4-Cyanophenyl)-2,3-dihydro-imidazo[2,1-b]thiazole-5-carboxylic acid hydrochloride

Product 1

HCID 70121114N-(2-Phenylthio-1-ethyl) 3-(4-Cyanophenyl)-2,3-dihydro-imidazo[2,1-b]thiazole-5-carboxamide hydrochloride

Procedure

The carboxylic acid from Step D, Example 1 (20.0 mg, 0.0625 mmol), 2-aminoethyl phenyl sulfide (9.6 mg, 0.0625 mmol), EDC hydrochloride (14.4 mg, 0.0751 mmol), HOBT (10.1 mg, 0.0751 mmol), and N,N-diisopropylethylamine (0.044 mL, 0.250 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=407. 1H-NMR (CD3OD): δ7.77 (s, 1H); 7.74 (d, 2H, J=8.3 Hz); 7.25-7.33 (m, 6H); 7.18 (t, 2H, J=7.2 Hz); 6.44 (bd, 1H, J=8.6 Hz); 4.77 (dd, 1H, J=11.8, 8.9 Hz); 3.91 (d, 1H, J=11.8 Hz), 3.40 (ddd, 2H, J=13.6, 6.8, 4.3 Hz); 3.00 (t, 2H, J=6.8 Hz).

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-815708992075445481b827b552fce1d2
Source dataset
uspto-grants-2002_04
Patent number
US06380228B1

Reaction notes

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