Acetic Acid → HCID 178437419, compound

HRID 1729440Notes

Reaction equation

HRID 1729440 reaction equation
C(C1[N:8]=[C:7]2[N:9]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[C:27]4[NH:31][N:30]=[N:29][N:28]=4)=[CH:17][CH:16]=3)[C:10]([CH2:12][CH3:13])=[N:11][C:6]2=[C:5]([CH3:32])[CH:4]=1)#N.[Br-].[CH3:34][C:35]([OH:37])=O.[CH2:38]1COCC1>>[C:35]([C:34]1[N:8]=[C:7]2[N:9]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[C:27]4[NH:31][N:30]=[N:29][N:28]=4)=[CH:17][CH:16]=3)[C:10]([CH2:12][CH3:13])=[N:11][C:6]2=[C:5]([CH3:32])[CH:4]=1)(=[O:37])[CH3:38]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 259Bromide ionHCID 8028TetrahydrofuranHCID 178437440HCID 178437440, compound

Product 1

HCID 178437419HCID 178437419, compound

Conditions

Temperature
50 °C

Procedure

To 5-Cyano-2-ethyl-7-methyl-3-(2'-(tetrazol-5-yl)biphen-4-yl)methyl-3H-imidazo[4,5-b]pyridine (137 mg) at 0° C. in THF (5 mL) was added methylmagne slum bromide (0.70 mL, 3M/ether). After stirring for 6 hour, 10 % aqueous HOAc was added, the mixture was heated to 50° C. for 10 minutes then extracted w ith EtOAc. Purification (SiO2, 93/3/4 CH2Cl2 /MeOH/HOAc) gave 40 mg of the title compound. 1H NMR (300 MHz, CD3OD) 7.88 (s, 1H), 7.67-7.60 (m, 2 H), 7.58-7.50 (m, 2 H), 7.28-7.05 (AB quartet, 4H), 5.63 (s, 2H), 2.95 (q, 2H, J=7.5 Hz), 2.70 (s, 3H), 2.68 (s, 3H), 130 (t, 3H, J=7.5 Hz)

Workup

  1. extractionthen extracted w ith EtOAc
  2. customPurification (SiO2, 93/3/4 CH2Cl2 /MeOH/HOAc)

Sources & evidence

ORD record
ord-4642a16776f642c496e25546c3b87796
Source dataset
uspto-grants-1994_07
Patent number
US05332744

Reaction notes

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