HRID1190535

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID10340

Carbonic acid sodium salt (1:2)

CNa2O3

结构：CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21

HCID636044

1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)

C39H32OP2

HCID17749886

2-(Methanesulfonyl)ethan-1-amine--hydrogen chloride (1/1)

C3H10ClNO2S

结构：CN(C(=O)c1cc2c(s1)-c1ccc(Br)cc1OCC2)c1cc(C(=O)N2CCN(C(=O)OC(C)(C)C)CC2)ccc1Cl

HCID58204000

未命名化合物

PRODUCTS

生成物

结构：CN(C(=O)c1cc2c(s1)-c1ccc(C(=O)NCCS(C)(=O)=O)cc1OCC2)c1cc(C(=O)N2CCN(C(=O)OC(C)(C)C)CC2)ccc1Cl

HCID58204219

未命名化合物

收率 629.8%

AUXILIARIES

试剂、催化剂与溶剂

催化剂HCID167845

Diacetatopalladium

C4H6O4Pd

溶剂HCID1140

Toluene

C7H8

CONDITIONS

反应条件

温度: 80 °C

PROCEDURE

实验过程

A suspension of tert-butyl 4-(3-(8-bromo-N-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamido)-4-chlorobenzoyl)piperazine-1-carboxylate (500 mg, 0.76 mmol), Pd(OAc)2 (9 mg, 0.038 mmol), Xantphos (44 mg, 0.076 mmol), MeSO2(CH2)2NH2.HCl (182 mg, 1.14 mmol) and Na2CO3 (242 mg, 2.28 mmol) in toluene (10 mL) was heated at 80° C. under atmosphere of CO from balloon for overnight. Then it was filtrated and concentrated, the crude product was purified by pre-TLC (DCM:MeOH=10:1 as eluted solvent) to give tert-butyl 4-(4-chloro-3-(N-methyl-8-(2-(methylsulfonyl)ethylcarbamoyl)-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamido)benzoyl)piperazine-1-carboxylate (350 mg, yield 63%). 1H NMR (CDCl3, 400 MHz): δ 7.60-7.34 (m, 8H, ArH, NH), 4.26-2.80 (m, 22H, CH2, CH3), 1.48 (s, 9H, 3CH3).

WORKUP

后处理

filtrationThen it was filtrated
concentrationconcentrated
customthe crude product was purified by pre-TLC (DCM:MeOH=10:1 as eluted solvent)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-5ec3bf8ee7d047889bac8f7684d532cf
来源数据集: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08673952B2
来源说明: uspto-grants-2014_03

反应 SMILES

Br[C:2]1[CH:3]=[CH:4][C:5]2[C:11]3[S:12][C:13]([C:15]([N:17]([C:19]4[CH:20]=[C:21]([CH:37]=[CH:38][C:39]=4[Cl:40])[C:22]([N:24]4[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]4)=[O:23])[CH3:18])=[O:16])=[CH:14][C:10]=3[CH2:9][CH2:8][O:7][C:6]=2[CH:41]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)[O:63][C:45]2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.[CH3:84][S:85]([CH2:88][CH2:89][NH2:90])(=[O:87])=[O:86].Cl.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:40][C:39]1[CH:38]=[CH:37][C:21]([C:22]([N:24]2[CH2:25][CH2:26][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:28][CH2:29]2)=[O:23])=[CH:20][C:19]=1[N:17]([CH3:18])[C:15]([C:13]1[S:12][C:11]2[C:5]3[CH:4]=[CH:3][C:2]([C:45](=[O:63])[NH:90][CH2:89][CH2:88][S:85]([CH3:84])(=[O:87])=[O:86])=[CH:41][C:6]=3[O:7][CH2:8][CH2:9][C:10]=2[CH:14]=1)=[O:16]