m-Aminoacetanilide → HCID 66712906, compound

HRID 1262440Notes

Reaction equation

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

Participants

Reactant 2

HCID 7604m-Aminoacetanilide

HCID 178450409HCID 178450409, compound

Product 1

HCID 66712906HCID 66712906, compoundYield 39%

Procedure

Analogous to Example 1510b, 7-(3-tert-Butoxymethyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ol (109 mg, 0.37 mmol) and 3′-aminoacetanilide (0.0689 g, 0.459 mmol) were reacted to afford N-{3-[7-(3-tert-Butoxymethyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-phenyl}-acetamide as an orange foam (62 mg, 39%). LCMS: 430 (M+H); 1H-NMR (DMSO-d6): 9.84 (s, 1H), 9.46 (s, 1H), 8.98 (s, 1H), 8.12 (s, 1H), 8.06 (d, 1H, J=7.71 Hz), 7.72 (s, 1H), 7.63 (d, 1H, J=7.71 Hz), 7.44 (t, 1H, J=7.71 Hz), 7.35 (d, 1H, J=7.71 Hz), 7.22 (m, 2H), 7.19 (d, 1H, 4.65 Hz), 6.96 (d, 1H, J=4.65 Hz), 4.46 (s, 2H), 2.03 (s, 3H), 1.22 (s, 9H).

Sources & evidence

ORD record: ord-2270a56152cb444fb2b27d9ce4c7fc84
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08471005B2

Reaction notes

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