1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 6-{(E)-2-[2-(2,2-Dimethylpropoxy)-3-methoxyphenyl]vinyl}-N-[4-(tert-butyl)-1,3-thiazol-2-yl]imidazo[2,1-b][1,3]thiazole-5-carboxamide

HRID 1882153Notes

Reaction equation

HRID 1882153 reaction equation
[CH3:1][C:2]([CH3:27])([CH3:26])[CH2:3][O:4][C:5]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:6]=1/[CH:13]=[CH:14]/[C:15]1[N:16]=[C:17]2[N:21]([C:22]=1[C:23]([OH:25])=O)[CH:20]=[CH:19][S:18]2.[C:28]([C:32]1[N:33]=[C:34]([NH2:37])[S:35][CH:36]=1)([CH3:31])([CH3:30])[CH3:29].CCN=C=NCCCN(C)C.Cl>CN(C1C=CN=CC=1)C.C(Cl)Cl.CN(C=O)C>[CH3:27][C:2]([CH3:1])([CH3:26])[CH2:3][O:4][C:5]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:6]=1/[CH:13]=[CH:14]/[C:15]1[N:16]=[C:17]2[N:21]([C:22]=1[C:23]([NH:37][C:34]1[S:35][CH:36]=[C:32]([C:28]([CH3:31])([CH3:30])[CH3:29])[N:33]=1)=[O:25])[CH:20]=[CH:19][S:18]2

Participants

7

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27342024-tert-Butyl-1,3-thiazol-2-amineHCID 675494856-{(E)-2-[2-(2,2-Dimethylpropoxy)-3-methoxyphenyl]vinyl}imidazo[2,1-b][1,3]thiazole-5-carboxylic acid

Product 1

HCID 468326576-{(E)-2-[2-(2,2-Dimethylpropoxy)-3-methoxyphenyl]vinyl}-N-[4-(tert-butyl)-1,3-thiazol-2-yl]imidazo[2,1-b][1,3]thiazole-5-carboxamide

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared according to the general procedure (Method B) by coupling Intermediate 3 (150 mg, 0.388 mmol) with 4-tert-butyl-1,3-thiazol-2-amine (72 mg, 0.465 mmol) in the presence of EDCI hydrochloride (148 mg, 0.776 mmol) and DMAP (71 mg, 0.582 mmol) in a mixture of DCM and DMF (4:1, 10 mL) to give 70 mg of the product as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ 1.06 (s, 9H), 1.33 (s, 9H), 3.57 (s, 2H), 3.80 (s, 3H), 6.58 (s, 1H), 6.98 (d, J=8.1 Hz, 1H), 7.10 (t, J=7.8 Hz, 1H), 7.32-7.34 (m, 1H), 7.41 (d, J=4.5 Hz, 1H), 7.87 (d, J=16.8 Hz, 1H), 8.11 (d, J=16.5 Hz, 1H), 8.79 (d, J=3.9 Hz, 1H), 12.68 (br s, 1H); ESI-MS (m/z) 525.43 (MH)+.

Sources & evidence

ORD record
ord-c03a2905f4e14007a6549e0293126312
Source dataset
uspto-grants-2012_11
Patent number
US08318928B2

Reaction notes

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