1-Hydroxybenzotriazole → HCID 46926697, compound

HRID 1891106Notes

Reaction equation

HRID 1891106 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]=[CH:20][C:21]=1[O:22][C:23]([F:26])([F:25])[F:24].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:32][C:29]3[S:30][CH:31]=[C:27]([C:18]4[CH:19]=[CH:20][C:21]([O:22][C:23]([F:26])([F:24])[F:25])=[C:16]([F:15])[CH:17]=4)[N:28]=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 57461636HCID 57461636, compoundHCID 710080931,3,5-trimethylthieno[3,4-d]pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 46926697HCID 46926697, 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-fluoro-4-(trifluoromethoxy)phenyl]-1,3-thiazol-2-amine (109 mg, 0.393 mmol) in the presence of EDCI hydrochloride (90 mg, 0.471 mmol), HOBt (16 mg, 0.117 mmol) and DMAP (5 mg, 0.039 mmol) in 1,2 dichloroethane (4 ml) to give 35 mg of the product as a 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), 7.64 (t, J=8.1 Hz, 1H), 7.80 (s, 1H), 7.85 (d, J=8.7 Hz, 1H), 7.93-8.01 (m, 1H), 12.45 (br s, 1H); APCI-MS (m/z) 515.02 (M+H)+.

Sources & evidence

ORD record
ord-f7ac380dd81341319f97fdb0767db2a1
Source dataset
uspto-grants-2013_08
Patent number
US08507503B2

Reaction notes

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