Diethylamine → HCID 11633937, compound

HRID 2114499Notes

Reaction equation

HRID 2114499 reaction equation
[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]

Participants

8

Reactant 4

HCID 8021DiethylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59809549HCID 59809549, compound2×

Product 2

HCID 11633937HCID 11633937, compoundYield 29%HCID 11641609HCID 11641609, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

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

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

Sources & evidence

ORD record
ord-eb21d20be7d3439e8b16a294dccbf1c0
Source dataset
uspto-grants-2008_10
Patent number
US07432257B2

Reaction notes

Loading…