1-Hydroxybenzotriazole → HCID 46926774, compound

HRID 877039Notes

Reaction equation

HRID 877039 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:17]=[C:18]([C:27]2[N:28]=[C:29]([NH2:32])[S:30][CH:31]=2)[CH:19]=[C:20]([F:26])[C:21]=1[C:22]([F:25])([F:24])[F:23].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>[F:15][C:16]1[CH:17]=[C:18]([C:27]2[N:28]=[C:29]([NH:32][C:39](=[O:54])[CH2:40][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:30][CH:31]=2)[CH:19]=[C:20]([F:26])[C:21]=1[C:22]([F:25])([F:23])[F:24]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57461652HCID 57461652, compoundHCID 710080931,3,5-trimethylthieno[3,4-d]pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 46926774HCID 46926774, 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-[3,5-difluoro-4-(trifluoromethyl)phenyl]-1,3-thiazol-2-amine (110 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 30 mg of the product as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ 3.19 (s, 3H), 3.47 (s, 3H), 4.07 (s, 2H), 7.07 (s, 1H), 7.83 (s, 1H), 7.87 (s, 1H), 8.06 (s, 1H), 12.51 (br s, 1H); APCI-MS (m/z) 517.01 (M+H)+.

Sources & evidence

ORD record
ord-4236e585b3e4425d8188cfe6242648a1
Source dataset
uspto-grants-2015_03
Patent number
US08987278B2

Reaction notes

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