Tert-Butylamine → HCID 136500844, compound

HRID 1056087Notes

Reaction equation

HRID 1056087 reaction equation
F[C:2]1[C:3]([CH3:22])=[N:4][C:5]2[C:10]([N:11]=1)=[C:9]([C:12]1[NH:21][C:15]3[N:16]=[CH:17][NH:18][C:19](=[O:20])[C:14]=3[CH:13]=1)[CH:8]=[CH:7][CH:6]=2.[C:23]([NH2:27])([CH3:26])([CH3:25])[CH3:24]>CS(C)=O>[C:23]([NH:27][C:2]1[C:3]([CH3:22])=[N:4][C:5]2[C:10]([N:11]=1)=[C:9]([C:12]1[NH:21][C:15]3[N:16]=[CH:17][NH:18][C:19](=[O:20])[C:14]=3[CH:13]=1)[CH:8]=[CH:7][CH:6]=2)([CH3:26])([CH3:25])[CH3:24]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 136500842HCID 136500842, compound

Product 1

HCID 136500844HCID 136500844, compoundYield 18.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Prepared similarly to that described in Example 260 using 6-(3-fluoro-2-methylquinoxalin-5-yl)-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one (Example 264; 60 mg, 0.203 mmol) and tert-butylamine (0.214 mL, 2.032 mmol) in DMSO (2 mL) at RT for 30 min. The mixture was purified with rpHPLC (Phenomenex Gemini C18 column (100×50 mm, 10 μm), 90 mL/min, 5-40% ACN in water with 0.1% TFA) to give 6-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one (13.0 mg, 0.037 mmol, 18% yield) as a yellow solid. MS (ESI, pos. ion) m/z: 349.1 (M+1); 1H NMR (400 MHz, DMSO-d6) δ ppm 12.34 (brs, 1H), 11.87 (brs, 1H); 7.99 (1H, d, J=6.8 Hz), 7.87 (1H, s), 7.66 (1H, d, J=7.0 Hz), 7.38 (1H, t, J=7.8 Hz), 7.27 (1H, s), 6.08 (1H, s), 2.57 (3H, s), 1.58 (9H, s).

Workup

  1. customPrepared similarly to that
  2. customThe mixture was purified with rpHPLC (Phenomenex Gemini C18 column (100×50 mm, 10 μm), 90 mL/min, 5-40% ACN in water with 0.1% TFA)

Sources & evidence

ORD record
ord-0a2a1afea2cd44d99b9183f2f30b394f
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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