HRID533487

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID10796

Cesium carbonate

CCs2O3

结构：c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1

HCID634876

2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl

C44H32P2

HCID58440201

未命名化合物

HCID66841440

未命名化合物

PRODUCTS

生成物

结构：NC(=O)c1cnc(Nc2ccc(F)c(NC(=O)N3CCCC3)c2)cc1NCc1cccnc1

HCID58098696

未命名化合物

收率 22.2%

AUXILIARIES

试剂、催化剂与溶剂

催化剂HCID167845

Diacetatopalladium

C4H6O4Pd

溶剂HCID31275

1,4-Dioxane

C4H8O2

PROCEDURE

实验过程

A mixture of 6-chloro-4-(pyridin-3-ylmethylamino)nicotinamide (2, 27 mg, 0.1 mmoles), N-(5-amino-2-fluorophenyl)pyrrolidine-1-carboxamide (3, 34 mg, 0.15 mmoles), Pd(OAc)2 (2 mg). BINAP (15 mg), Cs2CO3 (100 mg) in dioxane (1 mL) was heated at 120° C. under microwave for 60 min. Purification with reversed phase HPLC, 6-(4-fluoro-3-(pyrrolidine-1-carboxamido)phenylamino)-4-(pyridin-3-ylmethylamino)nicotinamide (4, 10 mg) was obtained. MS found for C23H24FN7O2 as (M+H)+ 450.5, UV: λ=249.1 nm. 1H NMR: (CD3OD) δ8.50 (s, 1H), δ8.42 (d, 1H), δ8.26 (d, 1H), δ7.80 (dd, 1H), δ7.60 (dd, 1H), δ7.40 (dd, 1H), δ7.00 (dd, 1H), δ6.91 (m, 1H), δ5.88 (d, 1H), δ4.49 (s, 2H), δ3.48 (m, 4H), δ1.99 (b, 4H).

WORKUP

后处理

customPurification with reversed phase HPLC

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-b82e99ec6c0949e5a80f430693a3f11e
来源数据集: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08853230B2
来源说明: uspto-grants-2014_10

反应 SMILES

Cl[C:2]1[CH:10]=[C:9]([NH:11][CH2:12][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[C:5]([C:6]([NH2:8])=[O:7])=[CH:4][N:3]=1.[NH2:19][C:20]1[CH:21]=[CH:22][C:23]([F:34])=[C:24]([NH:26][C:27]([N:29]2[CH2:33][CH2:32][CH2:31][CH2:30]2)=[O:28])[CH:25]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:34][C:23]1[CH:22]=[CH:21][C:20]([NH:19][C:2]2[CH:10]=[C:9]([NH:11][CH2:12][C:13]3[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=3)[C:5]([C:6]([NH2:8])=[O:7])=[CH:4][N:3]=2)=[CH:25][C:24]=1[NH:26][C:27]([N:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1)=[O:28]