Diisopropylethylamine → HCID 178499687, compound

HRID 1713937Notes

Reaction equation

HRID 1713937 reaction equation
FC(F)(F)C([O-])=O.[CH3:8][O:9][C:10](=[O:28])/[CH:11]=[CH:12]/[C:13]1[CH:27]=[CH:26][C:16]2[NH:17][C:18]([C:20]3([NH3+:25])[CH2:24][CH2:23][CH2:22][CH2:21]3)=[N:19][C:15]=2[CH:14]=1.[CH:29]1([C:35]2[C:43]3[C:38](=[CH:39][C:40]([C:44](O)=[O:45])=[CH:41][CH:42]=3)[N:37]([CH2:47][C:48]([N:50]([CH3:52])[CH3:51])=[O:49])[C:36]=2[C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1.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>[CH:29]1([C:35]2[C:43]3[C:38](=[CH:39][C:40]([C:44]([NH:25][C:20]4([C:18]5[NH:17][C:16]6[CH:26]=[CH:27][C:13](/[CH:12]=[CH:11]/[C:10]([O:9][CH3:8])=[O:28])=[CH:14][C:15]=6[N:19]=5)[CH2:24][CH2:23][CH2:22][CH2:21]4)=[O:45])=[CH:41][CH:42]=3)[N:37]([CH2:47][C:48]([N:50]([CH3:52])[CH3:51])=[O:49])[C:36]=2[C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 52754443-Cyclohexyl-1-dimethylcarbamoylmethyl-2-phenyl-1H-indole-6-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178499688HCID 178499688, compound

Product 1

HCID 178499687HCID 178499687, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-{5-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]-1H-benzimidazol-2-yl}cyclopentanaminium trifluoroacetate (from Step 4, 1 eq), 3-cyclohexyl-1-[2-(dimethylamino)-2-oxoethyl]-2-phenyl-1H-indole-6-carboxylic acid (from Example 1, Step 6, 1 eq) in DMF (0.02 M), HATU (1 eq) and DIPEA (5 eq) were added. The reaction mixture was left at RT with stirring overnight. The resulting mixture was partitioned between EtOAc and hydrochloric acid. The combined EtOAc layers were washed with saturated aqueous NaCl solution, separated, dried over Na2SO4, filtered and evaporated in vacuo to afford methyl (2E)-3-(2-{1-[({3-cyclohexyl-1-[2-(dimethylamino)-2-oxoethyl]-2-phenyl-1H-indol-6-yl}carbonyl)amino]cyclopentyl}-1H-benzimidazol-5-yl)acrylate, which was used without further purification. MS (ES+) m/z 672 (M+H)+.

Workup

  1. waitThe reaction mixture was left at RT
  2. customThe resulting mixture was partitioned between EtOAc and hydrochloric acid
  3. washThe combined EtOAc layers were washed with saturated aqueous NaCl solution
  4. customseparated
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-530c7cd18162468386e9e6d4a09a08dc
Source dataset
uspto-grants-2010_09
Patent number
US07795250B2

Reaction notes

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