1-(3-Aminophenyl)pyrrolidin-2-one → HCID 66712127, compound

HRID 1262359Notes

Reaction equation

HRID 1262359 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]([N:29]2[CH2:33][CH2:32][CH2:31][C:30]2=[O:34])[CH:26]=[CH:27][CH:28]=1>>[O:34]=[C:30]1[CH2:31][CH2:32][CH2:33][N:29]1[C:25]1[CH:24]=[C:23]([NH:22][C:4]2[N:9]=[CH:8][C:7]3=[CH:10][CH:11]=[C:12]([C:13]4[N:14]([CH2:18][CH2:19][C:20]#[N:21])[CH:15]=[CH:16][CH:17]=4)[N:6]3[N:5]=2)[CH:28]=[CH:27][CH:26]=1

Participants

3

Reactant 2

HCID 6839561-(3-Aminophenyl)pyrrolidin-2-oneHCID 66712602HCID 66712602, compound

Product 1

HCID 66712127HCID 66712127, compound

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 1-(3-amino-phenyl)-pyrrolidin-2-one (77 mg, 0.44 mmol) at 120° C. for 96 h to afford the title compound. Yield of TFA salt: 23 mg (15%) of brown powder. LC/MS: 412 (M+H); HPLC: 97% pure, RT=2.16 min; mp: 60-67° C.; 1H NMR: (DMSO, δ) 9.55 (s, 1H), 8.99 (s, 1H), 7.89 (s, 1H), 7.51 (d, J=8.2, 1H), 7.28 (d, J=8.2, 1H), 7.20 (t, J=8.1, 1H), 7.14 (m, 1H), 6.95 (d, J=4.5, 1H), 6.88 (d, J=4.4, 1H), 6.49 (dd, J=3.6, 1.5 1H), 6.27 (t, J=3.6, 1H), 4.19 (t, J=6.3, 2H), 3.49 (t, J=7.0, 2H), 2.77 (t, J=6.3, 2H), 2.47 (t, J=7.0, 2H), 2.02 (p, J=7.0, 2H).

Workup

  1. custompurification procedures

Sources & evidence

ORD record
ord-232f388b88d4494ea68fe42527ecc2b4
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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