Dimethylformamide → HCID 66712205, compound

HRID 1262413Notes

Reaction equation

[O:1]=[S:2]1(=[O:23])[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[CH:8]=[C:9]([C:13]2[N:21]3[C:16]([CH:17]=[N:18][C:19](O)=[N:20]3)=[CH:15][CH:14]=2)[CH:10]=[CH:11][CH:12]=1.C1C=CC(N(S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O)=CC=1.C(N(CC)C(C)C)(C)C.CN(C)C=O.[NH2:59][C:60]1[CH:68]=[C:67]2[C:63]([C:64]([CH3:71])([CH3:70])[C:65](=[O:69])[NH:66]2)=[CH:62][CH:61]=1>>[O:1]=[S:2]1(=[O:23])[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[CH:8]=[C:9]([C:13]2[N:21]3[C:16]([CH:17]=[N:18][C:19]([NH:59][C:60]4[CH:68]=[C:67]5[C:63]([C:64]([CH3:71])([CH3:70])[C:65](=[O:69])[NH:66]5)=[CH:62][CH:61]=4)=[N:20]3)=[CH:15][CH:14]=2)[CH:10]=[CH:11][CH:12]=1

Participants

Reactant 5

HCID 6228Dimethylformamide

HCID 81531Diisopropylethylamine

HCID 142176Phenyl triflimide

HCID 135892296-Amino-3,3-dimethyl-1,3-dihydro-2H-indol-2-one

HCID 178527142HCID 178527142, compound

Product 1

HCID 66712205HCID 66712205, compoundYield 57%

Conditions

Temperature: 65 °C

Procedure

7-[3-(1,1-dioxo-1,2-thiazolidin-2-yl)phenyl]pyrrolo[2,1-f][1,2,4]triazin-2-ol (47 mg, 0.14 mmol) and N-Phenylbis(trifluoromethanesulphonimide) (55.9 mg, 0.156 mmol) were treated with N,N-Diisopropylethylamine (0.100 mL, 0.575 mmol) and N,N-Dimethylformamide (3.00 mL, 38.7 mmol) for 30 min, then 6-Amino-3,3-dimethyl-1,3-dihydro-indol-2-one (31.3 mg, 0.178 mmol) was added and the mixture was stirred at 65° C. overnight. Conc. of the reaction gave a residue, which was chromatographed (silica gel, 20-100% EtOAc:Hex) to afford 6-({7-[3-(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 (39 mg; Yield=56%) as a yellow foam. LCMS (HPLC): 1.05 min, m/z=489 (M+H); 1H-NMR (DMSO-d6): 10.28 (s, 1H), 9.50 (s, 1H), 9.01 (s, 1H), 7.96 (d, 1H, J=7.8 Hz), 7.79 (s, 1H), 7.56 (m, 2H), 7.33 (d, 1H, J=8.3 Hz), 7.16 (m, 2H), 7.08 (s, 1H), 6.97 (d, 1H, J=4.7 Hz), 3.80 (t, 2H, J=6.5 Hz), 3.52 (t, 2H, J=7.4 Hz), 2.39 (m, 2H), 1.24 (s, 6H).

Workup

customConc. of the reaction gave a residue, which
customwas chromatographed (silica gel, 20-100% EtOAc:Hex)

Sources & evidence

ORD record: ord-f092545356c24570b7874fa324c7b7d2
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08471005B2

Reaction notes

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