1-Hydroxybenzotriazole → HCID 46927104, compound

HRID 1891114Notes

Reaction equation

HRID 1891114 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].[Br:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[S:26][C:25]([NH2:27])=[N:24][N:23]=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>[Br:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]2[S:26][C:25]([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)=[N:24][N:23]=2)=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 5542155-(4-Bromophenyl)-1,3,4-thiadiazol-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 46927104HCID 46927104, 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 5-(4-bromophenyl)-1,3,4-thiadiazol-2-amine (101 mg, 0.393 mmol) in the presence of EDCI hydrochloride (90 mg, 0.472 mmol), HOBt (16 mg, 0.118 mmol) and DMAP (5 mg, 0.039 mmol) in 1,2 dichloroethane (4 ml) to give 45 mg of the product as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ 3.18 (s, 3H), 3.47 (s, 3H), 4.11 (s, 2H), 7.09 (s, 1H), 7.72 (d, J=8.4 Hz, 2H), 7.87 (d, J=8.1 Hz, 2H), 12.85 (br s, 1H); APCI-MS (m/z) 493.93 (M+H)+.

Sources & evidence

ORD record
ord-a38ee5881fff4773bda18ae744aa6ed5
Source dataset
uspto-grants-2013_08
Patent number
US08507503B2

Reaction notes

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