m-Aminoacetanilide → HCID 66712746, compound

HRID 1262207Notes

Reaction equation

CS([C:4]1[N:9]=[CH:8][C:7]2=[CH:10][CH:11]=[C:12]([C:13]3[CH:14]=[C:15]([CH:23]=[CH:24][CH:25]=3)[CH2:16][N:17]([CH3:22])[S:18]([CH3:21])(=[O:20])=[O:19])[N:6]2[N:5]=1)=O.[NH2:26][C:27]1[CH:28]=[C:29]([CH:34]=[CH:35][CH:36]=1)[NH:30][C:31](=[O:33])[CH3:32]>>[CH3:21][S:18]([N:17]([CH2:16][C:15]1[CH:14]=[C:13]([C:12]2[N:6]3[C:7]([CH:8]=[N:9][C:4]([NH:26][C:27]4[CH:28]=[C:29]([NH:30][C:31](=[O:33])[CH3:32])[CH:34]=[CH:35][CH:36]=4)=[N:5]3)=[CH:10][CH:11]=2)[CH:25]=[CH:24][CH:23]=1)[CH3:22])(=[O:20])=[O:19]

Participants

Reactant 2

HCID 7604m-Aminoacetanilide

HCID 66712241HCID 66712241, compound

Product 1

HCID 66712746HCID 66712746, compound

Procedure

N-[3-(7-{3-[(Methanesulfonyl-methyl-amino)-methyl]-phenyl}-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino)-phenyl]-acetamide was prepared from N-[3-(2-methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-benzyl]-N-methyl-methanesulfonamide and 3′-aminoacetanilide in an analogous manner to Example 1049. Product isolated as a yellow foam (25 mg, 22%). LCMS (m/e) 465 (M+H); 1H-NMR (CDCl3, 400 MHz) δ 8.71 (s, 1H), 8.11 (d, 1H, J=7.7 Hz), 8.07 (s, 1H), 7.80 (s, 1H), 7.53-7.45 (m, 1H), 7.43-7.34 (m, 2H), 7.30 (s, 1H), 7.28-7.21 (m, 2H), 7.09 (s, 1H), 7.00 (d, 1H, J=4.8 Hz), 6.83 (d, 1H, J=4.8 Hz), 4.38 (s, 2H), 2.86 (s, 3H), 2.79 (s, 3H), 2.16 (s, 3H).

Sources & evidence

ORD record: ord-1f83327722a443d2ad30af776fe55537
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08471005B2

Reaction notes

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