4-Methoxybenzylamine → HCID 67126362, compound

HRID 706933Notes

Reaction equation

HRID 706933 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12](=[O:51])[C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:24][CH2:23][N:22]([CH2:25][C:26]4[CH2:31][CH2:30][C:29]([CH3:33])([CH3:32])[CH2:28][C:27]=4[C:34]4[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=4)[CH2:21][CH2:20]3)=[CH:15][C:14]=2[O:41][C:42]2[CH:43]=[C:44]3[CH:50]=[CH:49][NH:48][C:45]3=[N:46][CH:47]=2)(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:52]([O-:54])=[O:53].[CH3:55][O:56][C:57]1[CH:62]=[CH:61][C:60]([CH2:63][NH2:64])=[CH:59][CH:58]=1.CCN(C(C)C)C(C)C>CS(C)=O.CO>[Cl:40][C:37]1[CH:38]=[CH:39][C:34]([C:27]2[CH2:28][C:29]([CH3:32])([CH3:33])[CH2:30][CH2:31][C:26]=2[CH2:25][N:22]2[CH2:23][CH2:24][N:19]([C:16]3[CH:17]=[CH:18][C:13]([C:12]([NH:11][S:8]([C:5]4[CH:6]=[CH:7][C:2]([NH:64][CH2:63][C:60]5[CH:61]=[CH:62][C:57]([O:56][CH3:55])=[CH:58][CH:59]=5)=[C:3]([N+:52]([O-:54])=[O:53])[CH:4]=4)(=[O:10])=[O:9])=[O:51])=[C:14]([O:41][C:42]4[CH:43]=[C:44]5[CH:50]=[CH:49][NH:48][C:45]5=[N:46][CH:47]=4)[CH:15]=3)[CH2:20][CH2:21]2)=[CH:35][CH:36]=1

Participants

6

Reactant 3

HCID 754524-MethoxybenzylamineHCID 81531DiisopropylethylamineHCID 56591275HCID 56591275, compound

Product 1

HCID 67126362HCID 67126362, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Procedure

A suspension of EXAMPLE 53A (120 mg), (4-methoxyphenyl)methanamine (31 mg) and Hunig's Base (0.159 mL) in dimethylsulfoxide (2 mL) was heated for 2 hours at 150° C. in a Biotage Initiator microwave reactor. The reaction mixture was diluted with methanol (2 mL) and purified by reverse phase HPLC (C8, 30%-100% CH3CN/water/0.1% trifluoroacetic acid). 1H NMR (500 MHz, pyridine-d5) δ 13.07 (s, 1H), 9.32 (d, 1H), 9.17 (t, 1H), 8.43 (d, 1H), 8.28 (dd, 1H), 8.08 (d, 1H), 7.64-7.68 (m, 2H), 7.44 (d, 2H), 7.38 (d, 2H), 7.07 (d, 2H), 6.97-7.02 (m, 2H), 6.90 (d, 1H), 6.74 (dd, 1H), 6.52 (d, 1H), 6.49 (dd, 1H), 4.55 (d, 2H), 3.68 (s, 3H), 3.03-3.09 (m, 4H), 2.77 (s, 2H), 2.26 (t, 2H), 2.10-2.17 (m, 4H), 1.97 (s, 2H), 1.39 (t, 2H), 0.93 (s, 6H).

Workup

  1. custompurified by reverse phase HPLC (C8, 30%-100% CH3CN/water/0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-018e50f0fa014c9fa173100214a304ed
Source dataset
uspto-grants-2015_11
Patent number
US09174982B2

Reaction notes

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