Isoamyl Nitrite → HCID 59161259, compound

HRID 545529Notes

Reaction equation

HRID 545529 reaction equation
N[C:2]1[S:6][C:5]([C:7]2[CH:8]=[C:9]3[C:17](=[CH:18][CH:19]=2)[N:16]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=2)[C:15]2[CH2:14][CH2:13][C@@H:12]([NH:28][C:29](=[O:33])[CH:30]([CH3:32])[CH3:31])[CH2:11][C:10]3=2)=[N:4][N:3]=1.C(ON=O)CC(C)C>CN(C=O)C>[F:27][C:23]1[CH:22]=[C:21]([CH:26]=[CH:25][CH:24]=1)[CH2:20][N:16]1[C:15]2[CH2:14][CH2:13][C@@H:12]([NH:28][C:29](=[O:33])[CH:30]([CH3:32])[CH3:31])[CH2:11][C:10]=2[C:9]2[C:17]1=[CH:18][CH:19]=[C:7]([C:5]1[S:6][CH:2]=[N:3][N:4]=1)[CH:8]=2

Participants

4

Reactant 2

HCID 8053Isoamyl NitriteHCID 59161182HCID 59161182, compound

Product 1

HCID 59161259HCID 59161259, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Add (R)-N-[6-(5-Amino[1,3,4]thiadiazole-2-yl)-9-(3-fluorobenzyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]isobutyramide (Example 126) (0.104 g, 0.224 mmol) to a solution of isoamylnitrite (0.039 g, 0.337 mmol) in DMF at 60° C. and heat for 1 h. Quench reaction onto water and extract with EtOAc to give 80 mg of a yellow solid. Purify over silica eluting with 25-90% EtOAc/hexanes gradient to give 20 mg (20%). MS (ES) m/z 449 (M+1); 1H NMR (DMSO-d6): δ 9.56 (s, 1H), 8.08 (s, 1H), 7.89 (d, 1H), 7.77 (d, 1H), 7.57 (d, 1H), 7.38 (dd, 1H), 7.12 (dd, 2H), 6.84-6.94 (m, 2H), 5.44 (s, 2H), 4.05 (m, 1H), 3.07 (dd, 1H), 2.70-2.84 (m, 2H), 2.63 (m, 2H), 2.41 (septet, 1H), 2.00 (m, 1H), 1.88 (m, 1H), 1.04 (dd, 6H).

Workup

  1. temperatureheat for 1 h
  2. customQuench
  3. customreaction onto water
  4. extractionextract with EtOAc

Sources & evidence

ORD record
ord-912059a2ed634b1ba40d78a861176059
Source dataset
uspto-grants-2011_05
Patent number
US07935722B2

Reaction notes

Loading…