Diisopropylethylamine → HCID 59077583, compound

HRID 1359882Notes

Reaction equation

HRID 1359882 reaction equation
N1C2C(=NC=CC=2)N(O[C:11]([C:13]2[C:17]([CH3:18])=[C:16](/[CH:19]=[C:20]3\[C:21](=[O:41])[NH:22][C:23]4[C:28]\3=[CH:27][C:26]([S:29]([CH2:32][C:33]3[C:38]([Cl:39])=[CH:37][CH:36]=[CH:35][C:34]=3[Cl:40])(=[O:31])=[O:30])=[CH:25][CH:24]=4)[NH:15][C:14]=2[CH3:42])=[O:12])N=1.CCN(C(C)C)C(C)C.OC(C(F)(F)F)=O.[CH3:59][N:60]1[CH2:65][CH2:64][CH:63]([CH2:66][NH2:67])[CH2:62][CH2:61]1>CN(C=O)C>[CH3:59][N:60]1[CH2:65][CH2:64][CH:63]([CH2:66][NH:67][C:11]([C:13]2[C:17]([CH3:18])=[C:16](/[CH:19]=[C:20]3\[C:21](=[O:41])[NH:22][C:23]4[C:28]\3=[CH:27][C:26]([S:29]([CH2:32][C:33]3[C:38]([Cl:39])=[CH:37][CH:36]=[CH:35][C:34]=3[Cl:40])(=[O:30])=[O:31])=[CH:25][CH:24]=4)[NH:15][C:14]=2[CH3:42])=[O:12])[CH2:62][CH2:61]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 131724002HCID 131724002, compoundHCID 137178925HCID 137178925, compound

Product 1

HCID 59077583HCID 59077583, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-[5-(2,6-dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid [1,2,3]triazolo[4,5-b]pyridin-3-yl ester (300 mg, 0.48 mmol), DIPEA (136 mg, 2.2 eq.) and C-(1-methyl-piperidin-4-yl)-methylamine TFA salt (186 mg, 1.1 eq.) in DMF (5 mL) was stirred at rt for 72 hours. The reaction was concentrated, diluted with DCM, washed with sat.NaHCO3 and water, concentrated and purified on a silica gel column to give the titled compound as an orange solid.

Workup

  1. concentrationThe reaction was concentrated
  2. additiondiluted with DCM
  3. washwashed
  4. concentrationNaHCO3 and water, concentrated
  5. custompurified on a silica gel column

Sources & evidence

ORD record
ord-03b85cc0b6374816b0b5a65e52b0cb6c
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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