1-Hydroxybenzotriazole → HCID 46926698, compound

HRID 877036Notes

Reaction equation

HRID 877036 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:17]=[C:18]([C:23]2[N:24]=[C:25]([NH2:28])[S:26][CH:27]=2)[CH:19]=[CH:20][C:21]=1[Cl:22].CCN=C=NC[CH2:35][CH2:36]N(C)C.Cl.C1C=CC2N([OH:50])N=NC=2C=1>CN(C1C=CN=CC=1)C.ClCCCl>[Cl:15][C:16]1[CH:17]=[C:18]([C:23]2[N:24]=[C:25]([NH:28][C:35](=[O:50])[CH2:36][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:26][CH:27]=2)[CH:19]=[CH:20][C:21]=1[Cl:22]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 6185364-(3,4-Dichlorophenyl)-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 46926698HCID 46926698, compound

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-(3,4-dichlorophenyl)-1,3-thiazol-2-amine (96.5 mg, 0.393 mmol) in the presence of EDCI hydrochloride (90 mg, 0.471 mmol), HOBt (16 mg, 0.118 mmol) and DMAP (5 mg, 0.039 mmol) in 1,2 dichloroethane (4 ml) to give 40 mg of the product as a 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), 7.70 (d, J=8.4 Hz, 1H), 7.80 (s, 1H), 7.89 (d, J=6.9 Hz, 1H), 8.14 (s, 1H), 12.43 (br s, 1H); APCI-MS (m/z) 479.32 (M−H)+.

Sources & evidence

ORD record
ord-733c125ceb4d48dd9d557660f5015169
Source dataset
uspto-grants-2015_03
Patent number
US08987278B2

Reaction notes

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