Cyclobutylamine → HCID 59437532, compound

HRID 2382866Notes

Reaction equation

HRID 2382866 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([NH:11][C:12](=[O:19])[C:13]3[CH:18]=[CH:17][CH:16]=[N:15][CH:14]=3)[N:10]=[C:6]2[CH:5]=[C:4]([C:20]([F:23])([F:22])[F:21])[CH:3]=1.[CH:24]1([NH2:28])[CH2:27][CH2:26][CH2:25]1>>[CH:24]1([NH:28][C:2]2[N:7]3[N:8]=[C:9]([NH:11][C:12](=[O:19])[C:13]4[CH:18]=[CH:17][CH:16]=[N:15][CH:14]=4)[N:10]=[C:6]3[CH:5]=[C:4]([C:20]([F:23])([F:22])[F:21])[CH:3]=2)[CH2:27][CH2:26][CH2:25]1

Participants

3

Reactant 2

HCID 75645CyclobutylamineHCID 25212520HCID 25212520, compound

Product 1

HCID 59437532HCID 59437532, compoundYield 104.5%

Procedure

The title compound was prepared following procedure described for example 84, but starting from N-[5-chloro-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide ((B7), 100 mg; 0.3 mmol; 1.0 eq.) and cyclobutylamine (125 μl; 0.150 mmol; 5.0 eq.) at 120° C. for 30 min. under microwave irradiations. Solvents were removed under vacuum to dryness after which the residue was triturated with water, filtered and washed with EtOAc to give the title compound as a white powder (59 mg; 53%). 1H NMR (DMSO-d6) δ 11.4 (s, 1H), 9.15 (d, J=2.2 Hz, 1H), 8.79 (dd, J=1.5, 4.5 Hz, 1H), 8.35 (dt, J=1.8, 7.9 Hz, 1H), 7.63-7.56 (m, 2H), 7.32 (bs, 1H), 6.36 (d, J=1.5 Hz, 1H), 4.32-4.24 (m, 1H), 2.43-2.34 (m, 2H), 2.25-2.18 (m, 2H), 1.79-1.70 (m, 2H). HPLC, Rt: 3.20 min. (purity 94.8%). LC/MS, M+(ESI): 377.0, M−(ESI): 375.0.

Workup

  1. customThe title compound was prepared following procedure
  2. customSolvents were removed under vacuum to dryness after which the residue
  3. customwas triturated with water
  4. filtrationfiltered
  5. washwashed with EtOAc

Sources & evidence

ORD record
ord-21930a7ffde544318d8a0c20b1af0f74
Source dataset
uspto-grants-2012_09
Patent number
US08263595B2

Reaction notes

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