3,3-Difluoro-5-(8-morpholino-2-(2-(quinolin-2-yl)ethyl)imidazo[1,2-a]pyrazin-5-yl)indolin-2-one → Potassium 3,3-difluoro-5-(8-morpholino-2-(2-(quinolin-2-yl)ethyl)imidazo[1,2-a]pyrazin-5-yl)-2-oxoindolin-1-ide

HRID 1772667Notes

Reaction equation

[F:1][C:2]1([F:39])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[N:16]4[CH:17]=[C:18]([CH2:20][CH2:21][C:22]5[CH:31]=[CH:30][C:29]6[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=6)[N:23]=5)[N:19]=[C:15]4[C:14]([N:32]4[CH2:37][CH2:36][O:35][CH2:34][CH2:33]4)=[N:13][CH:12]=3)[CH:9]=2)[NH:4][C:3]1=[O:38].O(C)[K:41]>CO>[F:39][C:2]1([F:1])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[N:16]4[CH:17]=[C:18]([CH2:20][CH2:21][C:22]5[CH:31]=[CH:30][C:29]6[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=6)[N:23]=5)[N:19]=[C:15]4[C:14]([N:32]4[CH2:33][CH2:34][O:35][CH2:36][CH2:37]4)=[N:13][CH:12]=3)[CH:9]=2)[N-:4][C:3]1=[O:38].[K+:41]

Participants

Conditions

Temperature: 0 °C

Procedure

Compound 37c (65.3 mg, 0.124 mmol) was added to a MeOH solution of KOMe (8.69 mg, 0.124 mmol) at 0° C. The resulting mixture was stirred at 0° C. for 15 min, allowed to warm to rt, and stirred for another 30 min. The resulting mixture was concentrated and the resulting residue was dried under reduced pressure to obtain the title compound 59. 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 8.25 (d, J=8.6 Hz, 1H), 7.92 (d, J=8.3 Hz, 2H), 7.71 (t, J=7.7 Hz, 1H), 7.45-7.59 (m, 4H), 7.40 (br. s., 1H), 7.26 (s, 1H), 6.84 (d, J=7.6 Hz, 1H), 4.06 (m, 4H), 3.68 (m, 4H) 3.27-3.35 (m, 2H), 3.19-3.27 (m, 2H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C29H24F2N6O2: 527.2 (M+H). Found 527.5.

Workup

temperatureto warm to rt
stirringstirred for another 30 min
concentrationThe resulting mixture was concentrated
customthe resulting residue was dried under reduced pressure

Sources & evidence

ORD record: ord-5b33b9fcad724849bc97260239410c45
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249163B2

Reaction notes

Loading…