Diisopropylethylamine → tert-butyl N-[N-(5-propan-2-yl-1-quinolin-6-ylpyrazole-4-carbonyl)carbamimidoyl]carbamate

HRID 2298029Notes

Reaction equation

HRID 2298029 reaction equation
[CH:1]([C:4]1[N:8]([C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[N:15]=[CH:14][CH:13]=[CH:12]3)[N:7]=[CH:6][C:5]=1[C:19](O)=[O:20])([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[C:58]([O:62][C:63]([NH:65][C:66]([NH2:68])=[NH:67])=[O:64])([CH3:61])([CH3:60])[CH3:59]>CN(C)C=O>[C:58]([O:62][C:63]([NH:65][C:66]([NH:68][C:19]([C:5]1[CH:6]=[N:7][N:8]([C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[N:15]=[CH:14][CH:13]=[CH:12]3)[C:4]=1[CH:1]([CH3:2])[CH3:3])=[O:20])=[NH:67])=[O:64])([CH3:61])([CH3:59])[CH3:60]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 222676405-isopropyl-1-(6-quinolinyl)-1H-pyrazole-4-carboxylic acidHCID 178454308HCID 178454308, compound

Product 1

HCID 141011648tert-butyl N-[N-(5-propan-2-yl-1-quinolin-6-ylpyrazole-4-carbonyl)carbamimidoyl]carbamateYield 22.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-isopropyl-1-(6-quinolinyl)-1H-pyrazole-4-carboxylic acid (336.7 mg, 1.2 mmol) in 5 ml dimethylformamide was added N,N-diisopropylethylamine (0.42 ml, 2.39 mmol), benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (BOP reagent) (582 mg, 1.32 mmol) and tert-butoxycarbonylguanidine (210 mg, 1.32 mmol). The resulting solution was stirred at room temperature for 2 h, then heated to 60° C. for 2 h. The reaction mixture was then cooled to room temperature and concentrated to dryness in vacuo. The solid residue was partitioned between ethyl acetate and water. The ethyl acetate layer was washed with brine, dried (sodium sulfate) and concentrated to dryness in vacuo. The solid residue was triturated with methanol (1.5 ml), filtered, washed with diethyl ether and dried to yield the title compound as a white solid (114.3 mg, 22.5% yield).

Workup

  1. temperatureheated to 60° C. for 2 h
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. concentrationconcentrated to dryness in vacuo
  4. customThe solid residue was partitioned between ethyl acetate and water
  5. washThe ethyl acetate layer was washed with brine
  6. dry with materialdried (sodium sulfate)
  7. concentrationconcentrated to dryness in vacuo
  8. customThe solid residue was triturated with methanol (1.5 ml)
  9. filtrationfiltered
  10. washwashed with diethyl ether
  11. customdried

Sources & evidence

ORD record
ord-5e2897e223ae4cd482f37b408a653c35
Source dataset
uspto-grants-2002_12
Patent number
US06492401B1

Reaction notes

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