HRID2114499

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID8021

Diethylamine

C4H11N

HCID81531

Diisopropylethylamine

C8H19N

反应SMILES：CN(C)C(On1nnc2cccnc21)=[N+](C)C.F[P-](F)(F)(F)(F)F

HCID9886157

Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

C10H15F6N6OP

反应SMILES：COc1cccc2c1Oc1cc(C(=O)O)ccc1N2C1CCN(Cc2ccccc2)CC1

HCID59809549

未命名化合物

2 次

PRODUCTS

产物

反应SMILES：COc1cccc2c1Oc1cc(C(=O)N(C)C)ccc1N2C1CCN(Cc2ccccc2)CC1

HCID11633937

未命名化合物

收率 29%

反应SMILES：CCN(CC)C(=O)c1ccc2c(c1)Oc1c(OC)cccc1N2C1CCN(Cc2ccccc2)CC1

HCID11641609

未命名化合物

收率 28%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID962

Water

H2O

溶剂HCID6228

Dimethylformamide

C3H7NO

PROCEDURE

实验过程

To a solution of 10-(1-benzyl-piperidin-4-yl)-6-methoxy-10H-phenoxazine-3-carboxylic acid, 3d (240 mg, 0.56 mmol) in DMF was added HATU (424 mg, 1.11 mmol), N,N-diisopropyl-N-ethylamine (115 mg, 1.12 mmol), and N,N-diethylamine (82 mg, 1.12 mmol). The mixture was allowed to stir overnight at rt. Water (5 mL) was added, and the solution was extracted with EtOAc. The organic layer was separated, dried, and evaporated. The residue was purified via reverse phase HPLC (eluent: CH3CN in water containing 0.1% TFA) to yield 93.3 mg (28%) of 10-(1-benzyl-piperidin-4-yl)-6-methoxy-10H-phenoxazine-3-carboxylic acid diethylamide, 4d and 91.4 mg (29%) of 10-(1-benzyl-piperidin-4-yl)-6-methoxy-10H-phenoxazine-3-carboxylic acid dimethylamide, 5d, both as TFA salts (presence of 5d is presumably due to N,N-dimethylamine present in DMF). 4d: MS m/z (MH+) 486.0; 5d: MS m/z (MH+) 458.8.

WORKUP

后处理

extractionthe solution was extracted with EtOAc
customThe organic layer was separated
customdried
customevaporated
customThe residue was purified via reverse phase HPLC (eluent: CH3CN in water containing 0.1% TFA)

来源与证据

来源类型: Open Reaction Database
ORD记录: ord-eb21d20be7d3439e8b16a294dccbf1c0
来源数据集: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
专利号: US07432257B2
来源说明: uspto-grants-2008_10

反应SMILES

[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:27]3[CH:26]=[CH:25][C:24]([C:28]([OH:30])=[O:29])=[CH:23][C:22]=3[O:21][C:20]3[C:15]2=[CH:16][CH:17]=[CH:18][C:19]=3[O:31][CH3:32])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:33][N:34](C(ON1N=N[C:43]2C=[CH:45][CH:46]=[N:47][C:42]1=2)=[N+](C)C)[CH3:35].F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.C(NCC)C>CN(C=O)C.O>[CH2:46]([N:47]([CH2:42][CH3:43])[C:28]([C:24]1[CH:25]=[CH:26][C:27]2[N:14]([CH:11]3[CH2:10][CH2:9][N:8]([CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH2:13][CH2:12]3)[C:15]3[C:20]([O:21][C:22]=2[CH:23]=1)=[C:19]([O:31][CH3:32])[CH:18]=[CH:17][CH:16]=3)=[O:29])[CH3:45].[CH3:33][N:34]([CH3:35])[C:28]([C:24]1[CH:25]=[CH:26][C:27]2[N:14]([CH:11]3[CH2:12][CH2:13][N:8]([CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH2:9][CH2:10]3)[C:15]3[C:20]([O:21][C:22]=2[CH:23]=1)=[C:19]([O:31][CH3:32])[CH:18]=[CH:17][CH:16]=3)=[O:30]