1-Acetyl-6-aminoindoline → HCID 46852035, compound

HRID 1262137Notes

Reaction equation

HRID 1262137 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH2:13])[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].CS([C:17]1[N:22]=[CH:21][C:20]2=[CH:23][CH:24]=[C:25]([C:26]3[CH:27]=[C:28]([S:32]([N:35]4[CH2:39][CH2:38][C@H:37]([OH:40])[CH2:36]4)(=[O:34])=[O:33])[CH:29]=[CH:30][CH:31]=3)[N:19]2[N:18]=1)=O>CS(C)=O>[OH:40][C@H:37]1[CH2:38][CH2:39][N:35]([S:32]([C:28]2[CH:27]=[C:26]([C:25]3[N:19]4[C:20]([CH:21]=[N:22][C:17]([NH:13][C:10]5[CH:11]=[C:12]6[C:7]([CH2:6][CH2:5][N:4]6[C:1](=[O:3])[CH3:2])=[CH:8][CH:9]=5)=[N:18]4)=[CH:23][CH:24]=3)[CH:31]=[CH:30][CH:29]=2)(=[O:34])=[O:33])[CH2:36]1

Participants

4

Reactant 2

HCID 2585641-Acetyl-6-aminoindolineHCID 66712029HCID 66712029, compound

Product 1

HCID 46852035HCID 46852035, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1-acetyl-6-aminoindoline and (S)-1-[3-(2-Methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-benzenesulfonyl]-pyrrolidin-3-ol were reacted in an analogous manner to Example 881D. The mixture was then taken up in DMSO and purified by Gilson prep HPLC to afford the product as a TFA salt (16 mg, 17%). HPLC purity=94%, rt=2.636 min, LCMS=519.2 (M+H). 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.41 (s, 1H0, 9.01 (s, 1H), 8.58 (d, J=8.3 Hz, 1H), 8.31 (s, 1H), 8.26 (s, 1H0, 7.76 (d, J=8.1 Hz, 1H), 7.68 (dd, J=8.1 Hz, 8.1 Hz, 1H), 7.52 (dd, J=8.3 Hz, 1.8 Hz, 1H), 7.27 (d, J=4.7 Hz, 1H), 7.19 (d, J=8.3 Hz, 1H), 6.97 (d, J=4.9 Hz, 1H), 4.18-4.08 (m, 4H), 3.31-3.20 (m, 3H), 3.12-3.02 (m, 3H), 2.17 (s, 3H), 1.80-1.70 (m, 1H), 1.68-1.60 (m, 1H).

Workup

  1. custompurified by Gilson prep HPLC

Sources & evidence

ORD record
ord-7d1b94e87ad14f25a53d4c2af30e7ec4
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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