1-Hydroxybenzotriazole → 2-(1,3-Dimethyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-5-yl)-N-[4-(4-isobutylphenyl)-1,3-thiazol-2-yl]acetamide

HRID 1891100Notes

Reaction equation

HRID 1891100 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].[CH2:15]([C:19]1[CH:24]=[CH:23][C:22]([C:25]2[N:26]=[C:27]([NH2:30])[S:28][CH:29]=2)=[CH:21][CH:20]=1)[CH:16]([CH3:18])[CH3:17].CCN=C=NC[CH2:37][CH2:38]N(C)C.Cl.C1C=CC2N([OH:52])N=NC=2C=1>CN(C1C=CN=CC=1)C.ClCCCl>[CH3:1][N:2]1[C:10]2[S:9][CH:8]=[C:7]([CH2:37][C:38]([NH:30][C:27]3[S:28][CH:29]=[C:25]([C:22]4[CH:21]=[CH:20][C:19]([CH2:15][CH:16]([CH3:18])[CH3:17])=[CH:24][CH:23]=4)[N:26]=3)=[O:52])[C:6]=2[C:5](=[O:12])[N:4]([CH3:13])[C:3]1=[O:14]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 8698624-(4-Isobutylphenyl)-1,3-thiazol-2-amineHCID 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 469277722-(1,3-Dimethyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-5-yl)-N-[4-(4-isobutylphenyl)-1,3-thiazol-2-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 (100 mg, 0.393 mmol) with 4-(4-isobutylphenyl)-1,3-thiazol-2-amine (91 mg, 0.393 mmol) in the presence of EDCI hydrochloride (90 mg, 0.472 mmol), HOBt (16 mg, 0.117 mmol) and DMAP (5 mg, 0.039 mmol) in 1,2 dichloroethane (4 ml) to give 42 mg of the product as a white solid; 1H NMR (300 MHz, CDCl3) δ 0.88 (d, J=6.3 Hz, 6H), 1.83-1.90 (m, 1H), 2.48 (d, J=6.9 Hz, 2H), 3.51 (s, 3H), 3.57 (s, 3H), 4.06 (s, 2H), 6.88 (s, 1H), 7.04 (s, 1H), 7.16 (d, J=7.8 Hz, 2H), 7.72 (d, J=7.8 Hz, 2H), 10.73 (br s, 1H); APCI-MS (m/z) 469.14 (M+H)+.

Sources & evidence

ORD record
ord-71d729ddfe314b34876b93d080c32a24
Source dataset
uspto-grants-2013_08
Patent number
US08507503B2

Reaction notes

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