1-Hydroxybenzotriazole → HCID 46927842, compound

HRID 1891105Notes

Reaction equation

HRID 1891105 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].[F: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][C:17]=1[O:28][C:29]([F:32])([F:31])[F:30].CCN=C=NC[CH2:39][CH2:40]N(C)C.Cl.C1C=CC2N([OH:54])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]([CH2:39][C:40]([NH:27][C:24]3[S:25][CH:26]=[C:22]([C:19]4[CH:20]=[CH:21][C:16]([F:15])=[C:17]([O:28][C:29]([F:32])([F:30])[F:31])[CH:18]=4)[N:23]=3)=[O:54])[C:6]=2[C:5](=[O:12])[N:4]([CH3:13])[C:3]1=[O:14]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57461635HCID 57461635, compoundHCID 710080931,3,5-trimethylthieno[3,4-d]pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 46927842HCID 46927842, 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-[4-fluoro-3-(trifluoromethoxy)phenyl]-1,3-thiazol-2-amine (109 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 35 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), 7.59 (t, J=8.7 Hz, 1H), 7.76 (s, 1H), 8.00-8.06 (m, 2H), 12.44 (br s, 1H); APCI-MS (m/z) 513.11 (M−H)−.

Sources & evidence

ORD record
ord-cc3ab5874ff44a3fa177595038c80ffc
Source dataset
uspto-grants-2013_08
Patent number
US08507503B2

Reaction notes

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