m-Aminoacetanilide → N-(3-{7-[1-(2-Cyano-ethyl)-1H-pyrrol-2-yl]-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino}-phenyl)-acetamide

HRID 1262358Notes

Reaction equation

HRID 1262358 reaction equation
CS([C:4]1[N:9]=[CH:8][C:7]2=[CH:10][CH:11]=[C:12]([C:13]3[N:14]([CH2:18][CH2:19][C:20]#[N:21])[CH:15]=[CH:16][CH:17]=3)[N:6]2[N:5]=1)=O.[NH2:22][C:23]1[CH:24]=[C:25]([CH:30]=[CH:31][CH:32]=1)[NH:26][C:27](=[O:29])[CH3:28]>>[C:20]([CH2:19][CH2:18][N:14]1[CH:15]=[CH:16][CH:17]=[C:13]1[C:12]1[N:6]2[C:7]([CH:8]=[N:9][C:4]([NH:22][C:23]3[CH:24]=[C:25]([NH:26][C:27](=[O:29])[CH3:28])[CH:30]=[CH:31][CH:32]=3)=[N:5]2)=[CH:10][CH:11]=1)#[N:21]

Participants

3

Reactant 2

HCID 7604m-AminoacetanilideHCID 66712602HCID 66712602, compound

Product 1

HCID 66712232N-(3-{7-[1-(2-Cyano-ethyl)-1H-pyrrol-2-yl]-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino}-phenyl)-acetamide

Procedure

Following the synthetic and purification procedures described in Example 1293d, 3-[2-(2-methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-pyrrol-1-yl]-propionitrile (93 mg, 0.31 mmol) was coupled to 3′-aminoacetanilide (62 mg, 0.41 mmol) at 120° C. for 135 h to afford titled compound. Yield of TFA salt: 29 mg (19%) of gold powder. LC/MS: 386 (M+H); HPLC: 97% pure, RT=2.65 min; mp: 131-139° C.; 1H NMR: (DMSO, δ) 9.75 (s, 1H), 9.44 (s, 1H), 8.96 (s, 1H), 7.69 (s, 1H), 7.53 (d, J=7.4 ,1H), 7.12 (m, 3H), 6.95 (d, J=4.4, 1H), 6.90 (d, J=4.4, 1H), 6.58 (dd, J=7.9, 3.6, 1H) 6.26 (dd, J=3.6, 3.4, 1H), 4.24 (t, J=6.3, 2H), 2.83 (t, J=6.3, 2H), 2.04 (s, 3H).

Workup

  1. custompurification procedures

Sources & evidence

ORD record
ord-c3deff37fede47028b6b30a1841f4df8
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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