Triethylamine hydrochloride → HCID 178517431, compound

HRID 1965692Notes

Reaction equation

HRID 1965692 reaction equation
[O:1]=[C:2]1[C:10]2([CH2:14][O:13][C:12]3[CH:15]=[C:16]4[C:20](=[CH:21][C:11]2=3)[CH2:19][CH2:18][O:17]4)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[CH2:22][C:23]1[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][CH:24]=1.[N-:31]=[N+:32]=[N-:33].[Na+].Cl.C(N(CC)CC)C>C1(C)C=CC=CC=1>[NH:31]1[C:27]([C:26]2[CH:25]=[CH:24][C:23]([CH2:22][N:3]3[C:4]4[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=4)[C:10]4([CH2:14][O:13][C:12]5[CH:15]=[C:16]6[C:20](=[CH:21][C:11]4=5)[CH2:19][CH2:18][O:17]6)[C:2]3=[O:1])=[CH:30][CH:29]=2)=[N:28][N:33]=[N:32]1

Participants

5

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 59352617HCID 59352617, compound

Product 1

HCID 178517431HCID 178517431, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A round bottom flask was charged with 4-[(2′-oxo-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-1′(2′H)-yl)methyl]benzonitrile (0.50 g, 1.27 mmol), sodium azide (0.21 g, 3.17 mmol), and triethylamine hydrochloride (0.45 g, 3.17 mmol) in toluene (20 mL). The reaction mixture was refluxed under argon for 24 h. After cooling to ambient temperature, the product was extracted with water. 36% hydrochloric acid was added dropwise to the aqueous layer. The solid was filtrated and dried under reduced pressure to afford 1′-[4-(1H-tetrazol-5-yl)benzyl]-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-2′(1′H)-one (0.38 g, 58%); 1H NMR (300 MHz, CDCl3) δ8.02 (d, J=8.0 Hz, 2H), 7.55 (d, J=8.0 Hz, 2H), 7.22 (t, J=7.6 Hz, 1H), 7.16 (d, J=7.6 Hz, 1H), 7.05-6.94 (m, 2H), 6.47 (s, 1H), 6.40 (s, 1H), 5.01 (ABq, 2H), 4.79 (ABq, 2H), 4.53-4.38 (m, 2H), 3.03-2.82 (m, 2H); 13C NMR (75 MHz, CD3OD) δ177.6, 161.6, 161.2, 142.5, 140.1, 132.6, 129.1, 128.6, 127.9, 124.2, 123.6, 120.8, 120.4, 119.4, 109.8, 92.9, 80.3, 72.5, 57.4, 43.3, 28.8; MS (ES+) m/z 437.9 (M+1).

Workup

  1. temperatureThe reaction mixture was refluxed under argon for 24 h
  2. extractionthe product was extracted with water
  3. addition36% hydrochloric acid was added dropwise to the aqueous layer
  4. filtrationThe solid was filtrated
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-2742bb86ef2f4b92aa2b42c1a589e307
Source dataset
uspto-grants-2013_04
Patent number
US08415370B2

Reaction notes

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