Methylamine → HCID 10346473, compound

HRID 968108Notes

Reaction equation

HRID 968108 reaction equation
[CH3:1][NH2:2].[O:3]1[C:7]2[CH:8]=[CH:9][C:10]([N:12]3[C:20]4[C:19]5[CH:21]=[C:22]([NH:25][C:26]([C:28]6[C:33]([Cl:34])=[CH:32][CH:31]=[C:30](Cl)[N:29]=6)=[O:27])[CH:23]=[CH:24][C:18]=5[CH2:17][CH2:16][C:15]=4[C:14]([C:36]([NH2:38])=[O:37])=[N:13]3)=[CH:11][C:6]=2[O:5][CH2:4]1>CC(N(C)C)=O>[O:3]1[C:7]2[CH:8]=[CH:9][C:10]([N:12]3[C:20]4[C:19]5[CH:21]=[C:22]([NH:25][C:26]([C:28]6[C:33]([Cl:34])=[CH:32][CH:31]=[C:30]([NH:2][CH3:1])[N:29]=6)=[O:27])[CH:23]=[CH:24][C:18]=5[CH2:17][CH2:16][C:15]=4[C:14]([C:36]([NH2:38])=[O:37])=[N:13]3)=[CH:11][C:6]=2[O:5][CH2:4]1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 22291830HCID 22291830, compound

Product 1

HCID 10346473HCID 10346473, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

The title compound was synthesized from N-methylamine (6 mL of 33 w % solution in EtOH) and the compound of Example 216 (1.04 g) by the same procedure used for Example 207 except that 1 mL of DMA was added. The reaction was carried out at 82° C. for 5 days. The title compound, isolated by preparative HPLC, is a white solid (0.29 g, 52%), M.p. 269-270° C. (decomposition). Its structure was confirmed by 1H NMR and LC/MS: 1H NMR (d6-DMSO): δ 2.76 (d, 3H, J=5.5 Hz), 2.84-3.99 (m, 4H), 6.16 (s, 2H), 6.57 (d, 1H, J=9 Hz), 6.91-7.04 (m, 3H), 7.12 (d, 1H, J=1 Hz), 7.22-7.34 (m, 3H), 7.46-7.54 (m, 3H), 10.19 (s, 1H). ESI mass spectrum for C26H22ClN6O4+: 517 (M+1).

Workup

  1. additionwas added

Sources & evidence

ORD record
ord-0fae031ac99042fb995ce37b42ceae4e
Source dataset
uspto-grants-2005_10
Patent number
US06956052B2

Reaction notes

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