Diisopropylethylamine → HCID 86623941, compound

HRID 1713936Notes

Reaction equation

HRID 1713936 reaction equation
N[C:2]1[CH:3]=[C:4](/[CH:9]=[CH:10]/[C:11]([O:13][CH3:14])=[O:12])[CH:5]=[CH:6][C:7]=1[NH2:8].[C:15]([O:19][C:20]([NH:22][C:23]1([C:28](O)=[O:29])[CH2:27][CH2:26][CH2:25][CH2:24]1)=[O:21])([CH3:18])([CH3:17])[CH3:16].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[C:15]([O:19][C:20]([NH:22][C:23]1([C:28]([NH:8][C:7]2[CH:6]=[CH:5][C:4](/[CH:9]=[CH:10]/[C:11]([O:13][CH3:14])=[O:12])=[CH:3][CH:2]=2)=[O:29])[CH2:27][CH2:26][CH2:25][CH2:24]1)=[O:21])([CH3:18])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 27346451-tert-Butoxycarbonylaminocyclopentanecarboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 53486922methyl (2E)-3-(3,4-diaminophenyl)prop-2-enoate

Product 1

HCID 86623941HCID 86623941, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl (2E)-3-(3,4-diaminophenyl)acrylate (from Step 3.1 eq), 1-[(tert-butoxycarbonyl)amino]cyclopentanecarboxylic acid (1 eq) in DMF (0.02 M), HATU (1 eq) and DIPEA (3 eq) were added. The reaction mixture was left at RT with stirring overnight. The resulting mixture was partitioned between EtOAc and HCl (1 N). The combined EtOAc layers were washed with brine, and the organic phase was dried over Na2SO4, separated, and evaporated in vacuo to afford methyl (2E)-3-{4-[({1-[(tert-butoxycarbonyl)amino]cyclopentyl}carbonyl)amino]phenyl}acrylate, which was used without further purification. MS (ES+) m/z 404 (M+H)+. The foregoing product was dehydrated by heating it at 65° C. in presence of acetic acid. (0.16 M); the reaction residue was purified by RP-HPLC (Conditions Symmetry (Waters) C18 Column, 7 micron, 19×300 mm; flow: 20 mL/min; Gradient: A H2O+0.1% TFA; B: MeCN+0.1% TFA; 70% A isocratic for 2 min., linear to 20% A in 16 min isocratic for 0.5 min. and linear to 10% A for 2 min). Fractions containing pure product were pooled and lyophilized to give methyl (2E)-3-(2-{1-[(tert-butoxycarbonyl)amino]-cyclopentyl}-1H-benzimidazol-5-yl)acrylate. MS (ES−) m/z 384 (M−H)−.

Workup

  1. waitThe reaction mixture was left at RT
  2. customThe resulting mixture was partitioned between EtOAc and HCl (1 N)
  3. washThe combined EtOAc layers were washed with brine
  4. dry with materialthe organic phase was dried over Na2SO4
  5. customseparated
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-a2caa052cadc4084b52846586b69ba23
Source dataset
uspto-grants-2010_09
Patent number
US07795250B2

Reaction notes

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