Diisopropylethylamine → HCID 22647811, compound

HRID 1179502Notes

Reaction equation

HRID 1179502 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=O)=[CH:4][C:3]1=[O:20].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.Cl.[NH2:55][C:56]1[CH:60]=[C:59]([C:61]([O:63][CH3:64])=[O:62])[N:58]([CH3:65])[CH:57]=1>CN(C=O)C.CCOCC>[CH3:65][N:58]1[C:59]([C:61]([O:63][CH3:64])=[O:62])=[CH:60][C:56]([NH:55][C:17](=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13][O:12][C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:2](=[O:1])[C:3](=[O:20])[CH:4]=2)=[CH:57]1

Participants

7

Reactant 4

HCID 81531Diisopropylethylamine2×HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 2794656methyl 4-amino-1-methyl-1H-pyrrole-2-carboxylate hydrochlorideHCID 226478225-[(1,2-Dioxo-1,2-dihydronaphth-4-yl)oxy]valeric Acid

Product 1

HCID 22647811HCID 22647811, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of an acid 503 (334 mg, 1.22 mmol) in DMF (1.67 mL) was treated with HBTU (462 mg, 1.22 mmol) followed by DIEA (452 mg, 3.5 mmol) and stirred for 5 min. 3-Amino-1-methyl-5-methyloxycarbonylpyrrol hydrochloride (232 mg, 1.22 mmol) and DIEA (378 mg, 3 mmol) were added to the reaction mixture. The latter was stirred for 2 h, diluted with Et2O, the precipitate was removed, dissolved in CHCl3, washed with 3% HCl, H2O, aqueous NaHCO3, H2O again, dried (MgSO4) and purified by chromatography on alumina column (CHCl3/MeOH 80:1, 50:1). The product was triturated with Et2O/CHCl3 to obtain a yellow-red solid (200 mg, 40%); mp 122-123° C. (decomp.): MS (LSIMS, 3-NBA) 410 (M+), 237 (M+−173). 1H NMR (CDCl3) 8.08 (d, J=7.5 Hz, 1H), 7.86 (d, J=7.3 Hz, 1H), 7.68 (t, J=7.5 Hz, 1H), 7.57 (t, J=7.5 Hz, 1H), 7.38 (d, J=1.8 Hz, 1H), 7.34 (s, 1H), 6.65 (d, J=2 Hz, 1H), 5.95 (s, 1H), 4.19 (t, J=5.53 Hz, 2H), 3.88 (s, 3H), 3.80 (s, 3H), 2.46 (t, J=6.6 Hz, 2H), 1.90-2.15 (m, 4H).

Workup

  1. stirringThe latter was stirred for 2 h
  2. customthe precipitate was removed
  3. dissolutiondissolved in CHCl3
  4. washwashed with 3% HCl, H2O, aqueous NaHCO3, H2O again
  5. dry with materialdried (MgSO4)
  6. custompurified by chromatography on alumina column (CHCl3/MeOH 80:1, 50:1)
  7. customThe product was triturated with Et2O/CHCl3

Sources & evidence

ORD record
ord-c2657263100a4c0891a7691f1f9d7f7a
Source dataset
uspto-grants-2007_10
Patent number
US07279502B2

Reaction notes

Loading…