Dimethylformamide dimethyl acetal → HCID 67072995, compound

HRID 2091691Notes

Reaction equation

HRID 2091691 reaction equation
[C:1]([C:4]1[S:8][C:7]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[C:6]([C:15]#[N:16])[C:5]=1[C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=1[Cl:24])(=[O:3])[CH3:2].CO[CH:27](OC)[N:28]([CH3:30])[CH3:29]>>[Cl:24][C:18]1[CH:19]=[C:20]([Cl:23])[CH:21]=[CH:22][C:17]=1[C:5]1[C:6]([C:15]#[N:16])=[C:7]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[S:8][C:4]=1[C:1](=[O:3])[CH:2]=[CH:27][N:28]([CH3:30])[CH3:29]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 67072685HCID 67072685, compound

Product 1

HCID 67072995HCID 67072995, compound

Procedure

A solution of 5-acetyl-4-(2,4-dichlorophenyl)-2-morpholin-4-ylthiophene-3-carbonitrile (52.3 mg, 0.000137 mol) in 1,1-dimethoxy-N,N-dimethylmethanamine (1.0 mL, 0.0075 mol) was flushed with argon and irradiated in microwave at 160° C. for 30 min. The reaction mixture was evaporated to dryness to give 4-(2,4-dichlorophenyl)-5-(3-(dimethylamino)acryloyl)-2-morpholinothiophene-3-carbonitrile as an intermediate. The above intermediate and hydrazine hydrate (30 mg, 0.0006 mol) in AcOH (1.5 mL, 0.026 mol) was irradiated in microwave at 120° C. for 15 min. The reaction mixture was evaporated and the residue was purified by column chromatography to afford 4-(2,4-dichlorophenyl)-2-morpholino-5-(1H-pyrazol-5-yl)thiophene-3-carbonitrile (19.5 mg, 84%). LCMS: (FA) ES+ 405.06, ES− 403.23; 1H NMR (400 MHz, d4-methanol) δ: 7.65 (d, 1H), 7.45 (m, 2H), 7.33 (d, 1H), 5.48 (s, 1H), 5.45 (br, 1H), 3.85 (m, 4H), 3.54 (m, 4H).

Workup

  1. customirradiated in microwave at 160° C. for 30 min
  2. customThe reaction mixture was evaporated to dryness

Sources & evidence

ORD record
ord-d7ced0c3c4e345228d1c1b026349796d
Source dataset
uspto-grants-2013_05
Patent number
US08440664B2

Reaction notes

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