Sodium bis(trimethylsilyl)amide → HCID 178419964, compound

HRID 1506070Notes

Reaction equation

HRID 1506070 reaction equation
C([N:8]1[CH:12]=[C:11]([C:13]2[N:18]=[CH:17][C:16]([NH2:19])=[C:15]([C:20]3[C:21](F)=[N:22][CH:23]=[C:24]([C:26]4[CH:31]=[CH:30][C:29]([CH2:32][N:33]5[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]5)=[CH:28][CH:27]=4)[CH:25]=3)[CH:14]=2)[N:10]=[N:9]1)C1C=CC=CC=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>O1CCCC1>[NH:8]1[CH:12]=[C:11]([C:13]2[N:18]=[CH:17][C:16]3[NH:19][C:21]4[N:22]=[CH:23][C:24]([C:26]5[CH:31]=[CH:30][C:29]([CH2:32][N:33]6[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]6)=[CH:28][CH:27]=5)=[CH:25][C:20]=4[C:15]=3[CH:14]=2)[N:10]=[N:9]1

Participants

4

Reactant 2

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 58266625HCID 58266625, compound

Product 1

HCID 178419964HCID 178419964, compoundYield 15.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6′-(1-benzyl-1H-1,2,3-triazol-4-yl)-2-fluoro-5-(4-piperidin-1-ylmethylphenyl)[3,4′]bipyridinyl-3′-ylamine (80 mg, 0.16 mmol) in anhydrous tetrahydrofuran (2 mL) was added sodium bis(trimethylsilyl)amide (1N solution in THF, 0.46 mL, 0.46 mmol) under a flow of nitrogen and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was then evaporated in vacuo to afford a residue that was purified by preparative HPLC (20-60% MeCN in water (0.1% ammonium hydroxide) over 30 min, 35 mL/min) to afford the title compound as an orange solid (10 mg, 10%). NMR (DMSO-D6, 500 MHz): 12.33 (s, 1H), 9.12 (s, 1H), 8.95 (s, 1H), 8.94 (d, J=2.2 Hz, 1H), 8.88 (s, 1H), 8.31 (s, 1H), 7.80 (d, J=8.1 Hz, 2H), 7.44 (d, J=8.0 Hz, 2H), 3.49 (s, 2H), 2.36 (s, 4H), 1.52 (m, 4H), 1.41 (m, 2H), triazole NH not observed. LCMS (Method D): RT=6.68 min, M+H+=410.

Workup

  1. customThe reaction mixture was then evaporated in vacuo
  2. customto afford a residue that
  3. customwas purified by preparative HPLC (20-60% MeCN in water (0.1% ammonium hydroxide) over 30 min, 35 mL/min)

Sources & evidence

ORD record
ord-ca1b1865d9d54f38912967f61811e2a8
Source dataset
uspto-grants-2015_12
Patent number
US09216980B2

Reaction notes

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