N-Methylaniline → HCID 58864155, compound

HRID 1353458Notes

Reaction equation

HRID 1353458 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][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=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>>[NH2:1][C:2]1[CH:11]=[C:10]([N:12]2[CH2:13][CH2:14][N:15]([C:18]([NH:20][CH2:21][C:22]([N:27]([CH3:26])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:23])=[O:19])[CH2:16][CH2:17]2)[C:9]2[C:4](=[CH:5][C:6]([Cl:25])=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 4

HCID 7515N-MethylanilineHCID 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 58864155HCID 58864155, compound

Procedure

As described for example 171, [[[4-(2-amino-7-chloro-4-quinolinyl)-1-piperazinyl]carbonyl]amino]-acetic acid, N-methyl-benzenamine, iPr2NEt, and HATU are reacted to afford the product. LC-MS: 452 (M++1). 1H NMR (CDCl3): δ 3.0–3.2 (m, 4H), 3.3 (s, 3H), 3.6–3.76 (m, 4H), 3.76–3.9 (d, 2H), 4.8–5.0 (s, 2H), 5.6–5.8 m, 1H), 6.1–6.2 (s, 1H), 7.13–7.18 (m, 1H), 7.2–7.25 (m, 2H), 7.36–7.48 (m, 3H), 7.6 (d, 1H), 7.68–7.72 (d, 1H).

Workup

  1. customare reacted
  2. customto afford the product

Sources & evidence

ORD record
ord-93d168ca4dee4e4b878043d03b71ccdd
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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