4-(2-Amino-1,3-thiazol-4-yl)benzonitrile → N-[4-(4-Cyanophenyl)-1,3-thiazol-2-yl]-6-{(E)-2-[2-(2,2-dimethylpropoxy)-3-methoxyphenyl]vinyl}imidazo[2,1-b][1,3]thiazole-5-carboxamide

HRID 1882156Notes

Reaction equation

HRID 1882156 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.[NH2:28][C:29]1[S:30][CH:31]=[C:32]([C:34]2[CH:41]=[CH:40][C:37]([C:38]#[N:39])=[CH:36][CH:35]=2)[N:33]=1.CCN=C=NCCCN(C)C.Cl>CN(C1C=CN=CC=1)C.C(Cl)Cl.CN(C=O)C>[C:38]([C:37]1[CH:36]=[CH:35][C:34]([C:32]2[N:33]=[C:29]([NH:28][C:23]([C:22]3[N:21]4[C:17]([S:18][CH:19]=[CH:20]4)=[N:16][C:15]=3/[CH:14]=[CH:13]/[C:6]3[CH:7]=[CH:8][CH:9]=[C:10]([O:11][CH3:12])[C:5]=3[O:4][CH2:3][C:2]([CH3:27])([CH3:1])[CH3:26])=[O:25])[S:30][CH:31]=2)=[CH:41][CH:40]=1)#[N:39]

Participants

7

Reactant 3

HCID 20495894-(2-Amino-1,3-thiazol-4-yl)benzonitrileHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 675494856-{(E)-2-[2-(2,2-Dimethylpropoxy)-3-methoxyphenyl]vinyl}imidazo[2,1-b][1,3]thiazole-5-carboxylic acid

Product 1

HCID 46834696N-[4-(4-Cyanophenyl)-1,3-thiazol-2-yl]-6-{(E)-2-[2-(2,2-dimethylpropoxy)-3-methoxyphenyl]vinyl}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 (130 mg, 0.336 mmol) with 4-(2-amino-1,3-thiazol-4-yl)benzonitrile (81 mg, 0.403 mmol) in the presence of EDCI hydrochloride (128 mg, 0.672 mmol) and DMAP (61 mg, 0.504 mmol) in a mixture of DCM and DMF (4:1, 5 mL) to give 27 mg of the product as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ 1.02 (s, 9H), 3.57 (s, 2H), 3.80 (s, 3H), 7.00 (d, J=8.4 Hz, 1H), 7.11 (t, J=7.8 Hz, 1H), 7.34 (d, J=7.2 Hz, 1H), 7.40-7.50 (m, 2H), 7.84 (s, 1H), 7.91-7.96 (m, 2H), 7.98-8.05 (m, 1H), 8.10-8.15 (m, 2H), 12.79 (br s, 1H); APCI-MS (m/z) 570.17 (MH)+.

Sources & evidence

ORD record
ord-060347c702b149249590ae5fb750cb96
Source dataset
uspto-grants-2012_11
Patent number
US08318928B2

Reaction notes

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