Benzylamine → HCID 10347873, compound

HRID 1353476Notes

Reaction equation

HRID 1353476 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:18]([NH:20][C@H:21]3[CH2:27][CH2:26][CH2:25][CH2:24][N:23]([CH2:28][C:29]([OH:31])=O)[C:22]3=[O:32])=[O:19])[CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][C:6]([Cl:33])=[CH:7][CH:8]=2)[N:3]=1.[CH2:34]([NH2:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>CN(C=O)C.C(OCC)(=O)C>[NH2:1][C:2]1[CH:11]=[C:10]([N:12]2[CH2:13][CH2:14][N:15]([C:18]([NH:20][C@H:21]3[CH2:27][CH2:26][CH2:25][CH2:24][N:23]([CH2:28][C:29]([NH:41][CH2:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)=[O:31])[C:22]3=[O:32])=[O:19])[CH2:16][CH2:17]2)[C:9]2[C:4](=[CH:5][C:6]([Cl:33])=[CH:7][CH:8]=2)[N:3]=1

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 10480044HCID 10480044, compound

Product 1

HCID 10347873HCID 10347873, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The mixtures of (3S)-[[[4-(2-amino-7-chloro-4-quinolinyl)-1-piperazinyl]carbonyl]amino]hexahydro-2-oxo-1H-azepine-1-acetic acid (50.0 mg, 0.1 mmol), benzyl amine (0.2 mL), HATU (50 mg), and diisopropylethyl amine (0.3 mL) in DMF (5 mL) was stirred at rt for 2 h. The reaction mixture was diluted with ethyl acetate (100 mL), washed with NaHCO3 (sat.) and water, dried over Na2SO4. Concentration in vacuo followed by flash chromatography afforded the title product. LC-MS: 564 (M++1). 1H NMR (CD3OD) δ 7.82 (d, 1H), 7.45 (s, 1H), 7.25 (m, 4H), 7.20 (m, 2H), 6.30 (s, 1H), 4.65 (d, 1H), 4.40 (s, 2H), 4.15 (m, 2H), 3.75 (m, 1H), 3.65 (m, 4H), 3.30 (m, 1H), 3.10 (m, 4H), 1.96 (m, 2H), 1.80 (m, 2H), 1.60 (m, 2H).

Workup

  1. washwashed with NaHCO3 (sat.) and water
  2. dry with materialdried over Na2SO4
  3. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-c63f2b645e17404b8448a0606247dcb2
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

Loading…