Diisopropylethylamine → HCID 22647811, compound

HRID 393871Notes

Reaction equation

HRID 393871 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 3 (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-68c9ba5baa204cee8e45ffdd0a0d55f2
Source dataset
uspto-grants-2004_10
Patent number
US06809176B2

Reaction notes

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