Ethanamine, 2,2,2-trifluoro- → HCID 59404973, compound

HRID 1099283Notes

Reaction equation

HRID 1099283 reaction equation
[NH2:1][C:2]1[C:7]2=[C:8]([C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20]([NH:22][C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[N:24]=4)=[O:21])=[CH:15][CH:14]=3)[CH:9]=[C:10]([CH:11]=O)[N:6]2[N:5]=[CH:4][N:3]=1.[F:33][C:34]([F:38])([F:37])[CH2:35][NH2:36].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[NH2:1][C:2]1[C:7]2=[C:8]([C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20]([NH:22][C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[N:24]=4)=[O:21])=[CH:15][CH:14]=3)[CH:9]=[C:10]([CH2:11][NH:36][CH2:35][C:34]([F:38])([F:37])[F:33])[N:6]2[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 9773Ethanamine, 2,2,2-trifluoro-HCID 5049666Sodium triacetoxyborohydrideHCID 59232186HCID 59232186, compound

Product 1

HCID 59404973HCID 59404973, compoundYield 36.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a suspension of N-[4-(4-amino-7-formylpyrrolo[2,1-f][1,2,4]triazin-5-yl)phenyl]-N′-[6-(trifluoromethyl)pyridin-2-yl]urea (5.0 mg, 0.011 mmol) in 1,2-dichloroethane (2 mL) was added 2,2,2-trifluoroethylamine (11.2 mg, 0.11 mmol), followed by sodium triacetoxyborohydride (24.0 mg, 0.11 mg). The mixture was stirred at rt under nitrogen for 4 d. The solvent was evaporated under reduced pressure. The residue was dissolved in DMF and purified by HPLC using a gradient of 20-90% MeCN in water to yield 2.1 mg (35%) of the title compound. 1H-NMR (DMSO-d6) 9.95 (bs, 1 H), 9.79 (bs, 1 H), 8.05-7.99 (m, 2 H), 7.90 (s, 1 H), 7.57 (d, J=8.6, 2 H), 7.50 (dd, J=6.4, 1.7, Hz, 1 H), 7.40 (d, J=8.6 Hz, 2 H), 6.66 (s, 1 H), 4.07 (d, J=6.8 Hz, 2 H), 3.30-3.23 (m, 2 H), 2.92-2.85 (m, 1 H); MS [M+H]+=525.1; LCMS RT=2.91 min.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in DMF
  3. custompurified by HPLC

Sources & evidence

ORD record
ord-aca4cfe25f9f4be9a939826057b75121
Source dataset
uspto-grants-2012_03
Patent number
US08143393B2

Reaction notes

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