Isoamyl Nitrite → HCID 59644538, compound

HRID 2252013Notes

Reaction equation

HRID 2252013 reaction equation
C(ON=O)CC(C)C.N[C:10]1[S:11][C:12]([C:41]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=2[Cl:49])=[O:42])=[C:13]([C:15]2[N:16]=[N:17][N:18]([CH2:26][C:27]3[CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[C:29]([C:37]([F:40])([F:39])[F:38])[CH:28]=3)[C:19]=2[C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[N:14]=1>C1COCC1.CCOC(C)=O>[F:40][C:37]([F:38])([F:39])[C:29]1[CH:28]=[C:27]([CH:32]=[C:31]([C:33]([F:36])([F:34])[F:35])[CH:30]=1)[CH2:26][N:18]1[C:19]([C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)=[C:15]([C:13]2[N:14]=[CH:10][S:11][C:12]=2[C:41]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=2[Cl:49])=[O:42])[N:16]=[N:17]1

Participants

5

Reactant 2

HCID 8053Isoamyl NitriteHCID 86601261HCID 86601261, compound

Product 1

HCID 59644538HCID 59644538, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add isoamylnitrite (29 μL, 0.21 mmol) to a solution of {2-amino-4-[1-(3,5-bis-trifluoromethyl-benzyl)-5-pyridin-3-yl-1H-[1,2,3]triazol-4-yl]-thiazol-5-yl}-(2-chloro-phenyl)-methanone (63 mg, 0.103 mmol) in THF (1.5 mL). Stir the solution at RT for 30 min. then warm to reflux for an additional 30 min. Cool solution to RT and dilute with EtOAc (30 mL). Wash the organic solution with saturated NaHCO3 (15 mL) and brine (15 mL) then dry, filter, and concentrate. Purify the crude material by flash chromatography then triturate with ether (2×0.3 mL) and dry to give the title compound: MS (IS) 594.1 (M+1), MS (ES−) 592.0 (M−1); 1HNMR (400 MHz, CDCl3): δ 9.17 (s, 1H), 8.60 (d, 1H, J=5.0), 8.50 (s, 1H), 7.97 (s, 1H), 7.76 (s, 1H), 7.65 (s, 2H), 7.41 (m, 2H), 7.24 (m, 2H), 7.19 (m, 1H), 5.77 (s, 2H).

Workup

  1. temperaturethen warm
  2. temperatureto reflux for an additional 30 min
  3. washWash the organic solution with saturated NaHCO3 (15 mL) and brine (15 mL)
  4. customthen dry
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify the crude material by flash chromatography
  8. customthen triturate with ether (2×0.3 mL)
  9. customdry

Sources & evidence

ORD record
ord-04eb5f33f1ab41da9a450fa880367620
Source dataset
uspto-grants-2008_01
Patent number
US07320994B2

Reaction notes

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