N-Methylbenzylamine → HCID 21101674, compound

HRID 1353455Notes

Reaction equation

HRID 1353455 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:18]([NH:20][CH2:21][C:22](O)=[O:23])=[O:19])[CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][C:6]([Cl:25])=[CH:7][CH:8]=2)[N:3]=1.[CH3:26][NH:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[NH2:1][C:2]1[CH:11]=[C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:18]([NH:20][CH2:21][C:22]([N:27]([CH3:26])[CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:23])=[O:19])[CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][C:6]([Cl:25])=[CH:7][CH:8]=2)[N:3]=1

Participants

6

Reactant 4

HCID 7669N-MethylbenzylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58864188HCID 58864188, compound

Product 1

HCID 21101674HCID 21101674, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of [[[4-(2-amino-7-chloro-4-quinolinyl)-1-piperazinyl]carbonyl]amino]-acetic acid (50 mg, 0.14 mmol), N-methylbenzylamine (0.022 mL, 0.17 mmol), iPr2NEt (0.07 mL, 0.50 mmol) in DMF (3 mL) was added HATU (68 mg, 0.18 mmol) and stirred at rt overnight. The reaction mixture was poured into ice-water, and the solid was collected by filtration. The solid was re-dissolved in CH2Cl2 and purified by preparative TLC (CH2Cl2-MeOH-Hexane, 8:2:2) affording the product as a light yellow powder. LC-MS: 467 (M++1). 1H NMR (CDCl3): δ 2.92 and 3.00 (each s, 3H), 3.05˜3.12 (m, 4H), 3.62˜3.72 (m, 4H), 4.12˜4.20 (m, 2H), 4.52 and 4.62 (each s, 2H), 5.08 (br.s, 2H), 5.94 (m, 1H), 6.15 (m, 1H), 7.14˜7.24 (m, 3H), 7.26˜7.40 (m, 3H), 7.58˜7.62 (m, 1H), 7.68˜7.72 (m, 1H).

Workup

  1. filtrationthe solid was collected by filtration
  2. dissolutionThe solid was re-dissolved in CH2Cl2
  3. custompurified by preparative TLC (CH2Cl2-MeOH-Hexane, 8:2:2)

Sources & evidence

ORD record
ord-7e2101fab4064af398c1358cc77f8f83
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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