2-Amino-4-(4-chlorophenyl)thiazole → N-[4-(4-Chlorophenyl)-1,3-thiazol-2-yl]-2-(1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-5-yl)acetamide

HRID 1891098Notes

Reaction equation

HRID 1891098 reaction equation
[CH3:1][N:2]1[C:7]2=[CH:8][S:9][C:10](C)=[C:6]2[C:5](=[O:12])[N:4]([CH3:13])[C:3]1=[O:14].[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[N:23]=[C:24]([NH2:27])[S:25][CH:26]=2)=[CH:18][CH:17]=1.CCN=C=NC[CH2:34][CH2:35]N(C)C.Cl.C1C=CC2N([OH:49])N=NC=2C=1>CN(C1C=CN=CC=1)C.ClCCCl>[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]2[N:23]=[C:24]([NH:27][C:34](=[O:49])[CH2:35][C:7]3[C:6]4[C:5](=[O:12])[N:4]([CH3:13])[C:3](=[O:14])[N:2]([CH3:1])[C:10]=4[S:9][CH:8]=3)[S:25][CH:26]=2)=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 732412-Amino-4-(4-chlorophenyl)thiazoleHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 710080931,3,5-trimethylthieno[3,4-d]pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 46927770N-[4-(4-Chlorophenyl)-1,3-thiazol-2-yl]-2-(1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-5-yl)acetamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 111,2-DichloroethaneSolvent

Procedure

The title compound was prepared according to the general procedure (Method A) by coupling Intermediate 1 (200 mg, 0.709 mmol) with 4-(4-chlorophenyl)-1,3-thiazol-2-amine (149 mg, 0.709 mmol) in the presence of EDCI hydrochloride (163 mg, 0.851 mmol), HOBt (28 mg, 0.212 mmol) and DMAP (8.60 mg, 0.079 mmol) in 1,2 dichloroethane (4 ml) to give 95 mg of the product as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ 3.19 (s, 3H), 3.47 (s, 3H), 4.06 (s, 2H), 7.07 (s, 1H), 7.50 (d, J=8.4 Hz, 2H), 7.66 (s, 1H), 7.92 (d, J=8.4 Hz, 2H), 12.41 (br s, 1H); APCI-MS (m/z) 445.27 (M+H)+.

Sources & evidence

ORD record
ord-a9aad6347c1e40728c41efffd82f1cfb
Source dataset
uspto-grants-2013_08
Patent number
US08507503B2

Reaction notes

Loading…