6-Amino-3,3-dimethyl-1,3-dihydro-2H-indol-2-one → HCID 66712661, compound

HRID 1262208Notes

Reaction equation

HRID 1262208 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:35]=[C:34]2[C:30]([C:31]([CH3:38])([CH3:37])[C:32](=[O:36])[NH:33]2)=[CH:29][CH:28]=1>>[CH3:37][C:31]1([CH3:38])[C:30]2[C:34](=[CH:35][C:27]([NH:26][C:4]3[N:9]=[CH:8][C:7]4=[CH:10][CH:11]=[C:12]([C:13]5[CH:14]=[C:15]([CH:23]=[CH:24][CH:25]=5)[CH2:16][N:17]([CH3:22])[S:18]([CH3:21])(=[O:20])=[O:19])[N:6]4[N:5]=3)=[CH:28][CH:29]=2)[NH:33][C:32]1=[O:36]

Participants

3

Reactant 2

HCID 135892296-Amino-3,3-dimethyl-1,3-dihydro-2H-indol-2-oneHCID 66712241HCID 66712241, compound

Product 1

HCID 66712661HCID 66712661, compound

Procedure

N-{3-[2-(3,3-Dimethyl-2-oxo-2,3-dihydro-1H-indol-6-ylamino)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-benzyl}-N-methyl-methanesulfonamide was prepared from N-[3-(2-methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-benzyl]-N-methyl-methanesulfonamide and 6-amino-3,3-dimethyl-1,3-dihydro-indol-2-one in an analogous manner to Example 1049. Product isolated as a yellow foam (23 mg, 19%). LCMS (m/e) 491 (M+H), 1H-NMR (CDCl3, 400 MHz) δ 8.73 (s, 1H), 8.11 (d, 1H, J=8.0 Hz), 8.09 (s, 1H), 7.56-7.52 (m, 1H), 7.52-7.46 (m, 1H), 7.44 (s, 1H), 7.35 (d, 1H, J=7.6 Hz), 7.10 (d, 1H, J=8.0 Hz), 7.05-6.98 (m, 2H), 6.93 (s, 1H), 6.86 (d, 1H, J=4.8 Hz), 4.41 (s, 2H), 2.90 (s, 3H), 2.83 (s, 3H), 1.40 (s, 6H).

Sources & evidence

ORD record
ord-07018c488f20467d915e34194af1e0b7
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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