5-amino-3,3-dimethylindolin-2-one → HCID 66711444, compound

HRID 1262435Notes

Reaction equation

HRID 1262435 reaction equation
[O:1]=[S:2]1(=[O:25])[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[N:21]2[C:16]([CH:17]=[N:18][C:19](S(C)=O)=[N:20]2)=[CH:15][CH:14]=1.[NH2:26][C:27]1[CH:28]=[C:29]2[C:33](=[CH:34][CH:35]=1)[NH:32][C:31](=[O:36])[C:30]2([CH3:38])[CH3:37]>>[O:1]=[S:2]1(=[O:25])[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[N:21]2[C:16]([CH:17]=[N:18][C:19]([NH:26][C:27]3[CH:28]=[C:29]4[C:33](=[CH:34][CH:35]=3)[NH:32][C:31](=[O:36])[C:30]4([CH3:38])[CH3:37])=[N:20]2)=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 221620915-amino-3,3-dimethylindolin-2-oneHCID 66712540HCID 66712540, compound

Product 1

HCID 66711444HCID 66711444, compoundYield 24%

Procedure

Analogous to Example 1491c, 7-[2-(1,1-Dioxido-1,2-thiazolidin-2-yl)phenyl]-2-(methylsulfinyl)pyrrolo[2,1-f][1,2,4]triazine (68 mg, 0.18 mmol) and 5-Amino-3,3-dimethyl-1,3-dihydro-indol-2-one (0.0637 g, 0.361 mmol) were reacted to afford 5-({7-[2-(1,1-Dioxido-1,2-thiazolidin-2-yl)phenyl]pyrrolo[2,1-f][1,2,4]triazin-2-yl}amino)-3,3-dimethyl-1,3-dihydro-2H-indol-2-one as a yellow solid (21 mg, 24%). LCMS: 489 (M+H); 1H-NMR (DMSO-d6): 10.12 (s, 1H), 9.24 (s, 1H), 8.94 (s, 1H), 7.86 (m, 1H), 7.63 (m, 1H), 7.53 (m, 1H), 7.28 (dd, 1H, J=8.53 Hz), 6.98 (d, 1H, J=4.93 Hz), 6.91 (d, 1H, J=4.93 Hz), 6.69 (d, 1H, J=8.53 Hz), 3.29 (s, 2H), 3.24 (t, 2H, J=7.69 Hz), 2.14 (quin, 2H, J=7.69 Hz), 1.05 (s, 6H).

Sources & evidence

ORD record
ord-07620b356fdd43f5a17b2ad5725e024e
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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