2-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-4-fluoro-6-(1-oxo-3,4,5,6,7,8-hexahydrobenzothieno[2,3-c]pyridin-2(1H)-yl)benzyl Acetate → 5-[5-Fluoro-2-(hydroxymethyl)-3-{(8-(5-(4-methylpiperazin-1-yl)pyridine-2-ylamino)imidazo[1,2-a]pyridin-6-yl)}phenyl]-8-thia-5-azatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-6-one

HRID 1024021Notes

Reaction equation

HRID 1024021 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:24]2[CH:25]=[C:26]([NH:33][C:34]3[CH:39]=[CH:38][C:37]([N:40]4[CH2:45][CH2:44][N:43]([CH3:46])[CH2:42][CH2:41]4)=[CH:36][N:35]=3)[C:27]3[N:28]([CH:30]=[CH:31][N:32]=3)[CH:29]=2)[C:5]([CH2:22][OH:23])=[C:6]([N:8]2[CH2:20][CH2:19]N3[C:12]4[CH2:13][CH2:14][CH2:15][CH2:16][C:17]=4[CH:18]=[C:10]3[C:9]2=[O:21])[CH:7]=1.C(OCC1C(N2CCC3C4CCCCC=4[S:66]C=3C2=O)=CC(F)=CC=1B1OC(C)(C)C(C)(C)O1)(=O)C.ClC1C=C(NC2C=CC(N3CCN(C)CC3)=CN=2)C2N(C=CN=2)C=1>>[F:1][C:2]1[CH:3]=[C:4]([C:24]2[CH:25]=[C:26]([NH:33][C:34]3[CH:39]=[CH:38][C:37]([N:40]4[CH2:45][CH2:44][N:43]([CH3:46])[CH2:42][CH2:41]4)=[CH:36][N:35]=3)[C:27]3[N:28]([CH:30]=[CH:31][N:32]=3)[CH:29]=2)[C:5]([CH2:22][OH:23])=[C:6]([N:8]2[C:9](=[O:21])[C:10]3[S:66][C:12]4[CH2:13][CH2:14][CH2:15][CH2:16][C:17]=4[C:18]=3[CH2:19][CH2:20]2)[CH:7]=1

Participants

4

Reactant 3

HCID 670162052-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-4-fluoro-6-(1-oxo-3,4,5,6,7,8-hexahydrobenzothieno[2,3-c]pyridin-2(1H)-yl)benzyl AcetateHCID 715538632-(5-Fluoro-2-(hydroxymethyl)-3-(8-(5-(4-methylpiperazin-1-yl)pyridin-2-ylamino)imidazo[1,2-a]pyridin-6-yl)phenyl)-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-1(2H)-oneHCID 86684119HCID 86684119, compound

Product 1

HCID 895424285-[5-Fluoro-2-(hydroxymethyl)-3-{(8-(5-(4-methylpiperazin-1-yl)pyridine-2-ylamino)imidazo[1,2-a]pyridin-6-yl)}phenyl]-8-thia-5-azatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-6-oneYield 35%

Procedure

Following the procedures as described for compound 101, 103g (499 mg, 1.0 mmol), and 6-chloro-N-(5-(4-methylpiperazin-1-yl)pyridin-2-yl)imidazo[1,2-a]pyridin-8-amine 101b (342 mg, 1.0 mmol) were reacted to give 103 as a white solid (220 mg, 35%). LCMS: [M+H]+ 638. 1H NMR (500 MHz, CDCl3) δ 8.22 (s, 2H), 7.96 (d, J=2.5, 1H), 7.83 (s, 1H), 7.63 (d, J=1.0, 1H), 7.57 (d, J=1.0, 1H), 7.30 (dd, J=3.0, 9.0, 1H), 7.24 (dd, J=2.5, 9.0, 1H), 7.03 (dd, J=3.0, 9.0, 1H), 6.92 (d, J=8.5, 1H), 4.57 (d, J=11.5, 1H), 4.35 (t, J=8.5, 1H), 4.21 (s, 1H), 4.09-4.15 (m, 1H), 3.87-3.92 (m, 1H), 3.16 (t, J=5.0, 4H), 2.85-3.02 (m, 4H), 2.60 (t, J=5.0, 4H), 2.51-2.57 (m, 2H), 2.37 (s, 3H), 1.85-1.95 (m, 4H)

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-5f98ecd986464f3793347db0570fcd13
Source dataset
uspto-grants-2014_05
Patent number
US08722676B2

Reaction notes

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