HCID 71253450, compound → HCID 86676704, compound

HRID 1775112Notes

Reaction equation

HRID 1775112 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:9]2[C:17]3[C:12](=[CH:13][N:14]=[C:15]([C:18]4[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=4)[CH:16]=3)[N:11]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[N:10]=2)=[N:6][C:7]=1F.Cl.[NH:33]1[CH2:39][CH2:38][CH2:37][C@@H:36]([NH:40][C:41](=[O:50])[O:42][CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH2:35][CH2:34]1>>[Br:1][C:2]1[C:7]([N:33]2[CH2:39][CH2:38][CH2:37][C@@H:36]([NH:40][C:41](=[O:50])[O:42][CH2:43][C:44]3[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=3)[CH2:35][CH2:34]2)=[N:6][C:5]([C:9]2[C:17]3[C:12](=[CH:13][N:14]=[C:15]([C:18]4[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=4)[CH:16]=3)[N:11]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[N:10]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 71253450HCID 71253450, compoundHCID 86676705HCID 86676705, compound

Product 1

HCID 86676704HCID 86676704, compound

Procedure

Following the procedures of Examples 241 and 287, 3-(5-bromo-6-fluoropyridin-2-yl)-5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridine and (R)-benzyl azepan-4-ylcarbamate hydrochloride were reacted to give (R)-benzyl 1-(3-bromo-6-(5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)azepan-4-ylcarbamate, which was dissolved in Trifluoroacetic Acid (5 mL) and Methylene chloride (5 mL), and treated with Trifluoromethanesulfonic acid (5 eq.) and Triethylsilane (5 eq.). The resulting mixture was stirred at room temperature for 2 days. The mixture was then concentrated, and the residue was purified by reverse phase HPLC to afford 313 as an off-white solid (14.2 mg, 25.5%) over two steps. 1H NMR (400 MHz, DMSO) δ 9.24 (s, 2H), 8.91 (s, 1H), 8.61 (d, J=3.6 Hz, 1H), 8.42 (d, J=8.0 Hz, 1H), 8.35 (s, 1H), 8.03 (d, J=8.0 Hz, 1H), 7.62-7.51 (m, 2H), 4.00 (d, J=14.6 Hz, 2H), 3.90-3.81 (m, 2H), 3.77 (dd, J=11.4, 6.7 Hz, 2H), 3.67-3.59 (m, 3H), 2.18 (s, 1H), 1.98 (dd, J=31.3, 18.3 Hz, 4H), 1.75-1.59 (m, 1H); ESI MS m/z=464.01 (M+1)

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-2dab46d71d924f67a945a8ae09d86eef
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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