Dimethylformamide → HCID 51347753, compound

HRID 2044334Notes

Reaction equation

HRID 2044334 reaction equation
C(Cl)(=O)C(Cl)=O.[Cl:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N:14]1[C:18]([C:19]2[N:20]=[C:21]3[C:27]4[CH:28]=[C:29]([C:32](O)=[O:33])[CH:30]=[CH:31][C:26]=4[O:25][CH2:24][CH2:23][N:22]3[CH:35]=2)=[N:17][CH:16]=[N:15]1.C[N:37](C)C=O.CN(C)C(=O)C>C(Cl)Cl.N>[Cl:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N:14]1[C:18]([C:19]2[N:20]=[C:21]3[C:27]4[CH:28]=[C:29]([C:32]([NH2:37])=[O:33])[CH:30]=[CH:31][C:26]=4[O:25][CH2:24][CH2:23][N:22]3[CH:35]=2)=[N:17][CH:16]=[N:15]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 31374DimethylacetamideHCID 65578Oxalyl chlorideHCID 58204972HCID 58204972, compound

Product 1

HCID 51347753HCID 51347753, compoundYield 349.8%

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 6344DichloromethaneSolvent2×

Procedure

Oxalyl chloride in methylene chloride (2.00 M, 3.0 mL) was added to a suspension of 2-(1-(2-chlorophenyl)-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-10-carboxylic acid (112 mg, 0.178 mmol) in 30 ml of methylene chloride. Catalytic amount of N,N-Dimethylformamide (1.0 uL, 0.013 mmol) was added and the mixture was stirred for 2 hours. The mixture was filtered, the filtrate was concentrated in vacuum and the residue dried in high vacuum for 1 hour. The above residue was dissolved in N,N-dimethylacetamide (3.0 mL, 32 mmol) and saturated with gaseous ammonia. The mixture was stirred for 20 min, concentrated in vacuum, dissolved in aqueous methanol and subjected to RP HPLC purification to yield 18.5 mg of 102 (26%), MS: 407.1. 1H NMR (400 MHz, DMSO) δ 8.26 (d, J=2.2, 1H), 8.20 (s, 1H), 7.80 (s, 1H), 7.72-7.51 (m, 6H), 7.29 (s, 1H), 7.00 (d, J=8.5, 1H).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuum
  3. customthe residue dried in high vacuum for 1 hour
  4. stirringThe mixture was stirred for 20 min
  5. concentrationconcentrated in vacuum
  6. dissolutiondissolved in aqueous methanol
  7. customsubjected to RP HPLC purification

Sources & evidence

ORD record
ord-006113f8a46c4e2180ae7889a6294d76
Source dataset
uspto-grants-2013_11
Patent number
US08586574B2

Reaction notes

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