Diisopropylethylamine → HCID 178489595, compound

HRID 2193779Notes

Reaction equation

HRID 2193779 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:12]2[S:20][C:19]3[C:14](=[N:15][CH:16]=[CH:17][C:18]=3[O:21][C:22]3[CH:27]=[CH:26][C:25]([NH:28][C:29](=[O:42])[CH2:30][C:31]([NH:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=4[O:40][CH3:41])=[O:32])=[CH:24][C:23]=3[F:43])[CH:13]=2)[CH:9]=[CH:10][CH:11]=1.[N:44]1([C:49](N)=[NH:50])C=CC=N1.CCN(C(C)C)C(C)C>CN(C=O)C.ClCCl.CO>[F:43][C:23]1[CH:24]=[C:25]([NH:28][C:29](=[O:42])[CH2:30][C:31]([NH:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[O:40][CH3:41])=[O:32])[CH:26]=[CH:27][C:22]=1[O:21][C:18]1[CH:17]=[CH:16][N:15]=[C:14]2[CH:13]=[C:12]([C:8]3[CH:9]=[CH:10][CH:11]=[C:6]([O:5][CH2:4][CH2:3][CH2:2][NH:1][C:49]([NH2:50])=[NH:44])[CH:7]=3)[S:20][C:19]=12

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 2734673PraxadineHCID 58790292HCID 58790292, compound

Product 1

HCID 178489595HCID 178489595, compoundYield 87.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

Amine 367 (0.095 g, 0.16 mmol), pyrazole-1-carboxamidine (60 mg, 0.41 mmol), and Hunigs base (0.07 g, 0.5 mmol) were stirred in dry DMF (10 mL) for 48 h at r.t. The mixture was then partitioned between ethyl acetate and water. The aqueous phase was collected and treated with brine; a precipitate was formed which was isolated by suction filtration. The resulting solid was re-dissolved in 1:1 dichloromethane/methanol, filtered, and the filtrate was concentrated to afford 361 as a solid (90 mg, 87% yield). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 10.71 (br s, 1H); 9.63 (br s, 1H); 8.49 (d, J=5.5, 1H); 8.10 (s, 1H); 8.05 (d, J=8.4, 1H); 7.93-7.70 (m, 2H); 7.51-7.40 (m, 5H); 7.08-7.02 (m, 3H); 6.92-6.88 (m, 1H); 6.63 (d, J=5.5, 1H); 4.13 (t, J=5.9, 2H); 3.84 (s, 3H); 3.64 (s, 2H); 1.95 (quint, J=6.3, 2H). [A triplet corresponding to 3H is hidden by the residial DMSO peak]. LRMS (M+H): 643.0.

Workup

  1. customThe mixture was then partitioned between ethyl acetate and water
  2. customThe aqueous phase was collected
  3. additiontreated with brine
  4. customa precipitate was formed which
  5. customwas isolated by suction filtration
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-3e3ab1d4cb22412084deed5b94de06c5
Source dataset
uspto-grants-2012_12
Patent number
US08329726B2

Reaction notes

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