Sodium hydride → tert-Butyl 4-(5-(2-nitro-5-(thiophen-2-yl)phenylcarbamoyl)thiophen-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 252874Notes

Reaction equation

HRID 252874 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[S:18][C:17]([C:19](O)=[O:20])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N+:22]([C:25]1[CH:30]=[CH:29][C:28]([C:31]2[S:32][CH:33]=[CH:34][CH:35]=2)=[CH:27][C:26]=1[NH2:36])([O-:24])=[O:23].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[H-].[Na+]>N1C=CC=CC=1>[N+:22]([C:25]1[CH:30]=[CH:29][C:28]([C:31]2[S:32][CH:33]=[CH:34][CH:35]=2)=[CH:27][C:26]=1[NH:36][C:19]([C:17]1[S:18][C:14]([C:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[CH2:13][CH:12]=2)=[CH:15][CH:16]=1)=[O:20])([O-:24])=[O:23]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 236564282-Nitro-5-(thiophen-2-yl)anilineHCID 597367605-(1-(Tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl)thiophene-2-carboxylic acid

Product 1

HCID 59736975tert-Butyl 4-(5-(2-nitro-5-(thiophen-2-yl)phenylcarbamoyl)thiophen-2-yl)-5,6-dihydropyridine-1(2H)-carboxylateYield 61%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Compound 353 (270 mg, 0.87 mmol), 2-nitro-5-(thiophen-2-yl)benzenamine (3, 193 mg, 0.87 mmol), and BOP (386 mg, 0.87 mmol) were dissolved in dry pyridine (10 mL). Sodium hydride (140 mg, 3.50 mmol) was added and the resulting solution was stirred at room temperature for 2 hours, quenched with glacial acetic acid (1 mL), and the pyridine was removed under reduced pressure. Water (50 mL) was added and the mixture was extracted with ethyl acetate (2×50 mL). The extract was dried with sodium sulphate and evaporated to yield a residue which was triturated with ethyl acetate for 15 minutes, to afford the title compound 354 as a yellow solid (270 mg, 61% yield). 1H NMR: (DMSO) δ 10.79 (s, 1H), 8.06-8.04 (m, 2H), 7.86 (d, J=3.9 Hz, 1H), 7.75-7.68 (m, 3H), 7.25-7.20 (m, 2H), 6.32 (s, 1H), 4.04-4.01 (m, 2H), 3.54 (t, J=5.3 Hz, 2H), 1.43 (s, 9H).

Workup

  1. customquenched with glacial acetic acid (1 mL)
  2. customthe pyridine was removed under reduced pressure
  3. additionWater (50 mL) was added
  4. extractionthe mixture was extracted with ethyl acetate (2×50 mL)
  5. dry with materialThe extract was dried with sodium sulphate
  6. customevaporated
  7. customto yield a residue which
  8. customwas triturated with ethyl acetate for 15 minutes

Sources & evidence

ORD record
ord-0045b27329f443adb567b91163174734
Source dataset
uspto-grants-2011_01
Patent number
US07868205B2

Reaction notes

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