1-Hydroxybenzotriazole → HCID 46926945, compound

HRID 877041Notes

Reaction equation

HRID 877041 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[O:26][N:25]=[C:24]([NH2:27])[CH: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[O:26][N:25]=[C:24]([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)[CH:23]=2)=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 162181875-(4-Bromophenyl)-1,2-oxazol-3-amineHCID 710080931,3,5-trimethylthieno[3,4-d]pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 46926945HCID 46926945, 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)isoxazol-3-amine (94 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 3.20 (s, 3H), 3.47 (s, 3H), 3.99 (s, 2H), 7.05 (s, 1H), 7.33 (s, 1H), 7.72 (d, J=8.1 Hz, 2H), 7.81 (d, J=8.4 Hz, 2H), 11.20 (br s, 1H); APCI-MS (m/z) 475.01 (M+H).

Sources & evidence

ORD record
ord-5bb831a6800945a59d3b58b91eedf82d
Source dataset
uspto-grants-2015_03
Patent number
US08987278B2

Reaction notes

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