1-Hydroxybenzotriazole → HCID 46926944, compound

HRID 1891111Notes

Reaction equation

HRID 1891111 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:21]=[CH:20][C:19]([C:22]2[CH:26]=[C:25]([NH2:27])[O: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>[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]2[CH: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)[O:24][N:23]=2)=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 21040623-(4-chlorophenyl)isoxazol-5-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 46926944HCID 46926944, 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 3-(4-chlorophenyl)isoxazol-5-amine (76 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 50 mg of the product as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ 3.20 (s, 3H), 3.47 (s, 3H), 4.01 (s, 2H), 6.67 (s, 1H), 7.07 (s, 1H), 7.55 (d, J=8.4 Hz, 2H), 7.85 (d, J=8.4 Hz, 2H), 11.90 (br s, 1H); APCI-MS (m/z) 429.17 (M−H)−.

Sources & evidence

ORD record
ord-e322a2ced6014ab08c3f59131de02922
Source dataset
uspto-grants-2013_08
Patent number
US08507503B2

Reaction notes

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