Diisopropylethylamine → HCID 66737367, compound

HRID 1640986Notes

Reaction equation

HRID 1640986 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[N:16]([C:20]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:15]=[C:14]3[NH2:39])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.C(N(CC)C(C)C)(C)C.Cl.[CH3:50][N:51]1[CH2:56][CH2:55][N:54]([C:57]2[CH:65]=[CH:64][C:60]([C:61](Cl)=[O:62])=[C:59]([N+:66]([O-:68])=[O:67])[CH:58]=2)[CH2:53][CH2:52]1>C(OCC)C>[F:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[N:16]([C:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:15]=[C:14]3[NH:39][C:61](=[O:62])[C:60]2[CH:64]=[CH:65][C:57]([N:54]3[CH2:55][CH2:56][N:51]([CH3:50])[CH2:52][CH2:53]3)=[CH:58][C:59]=2[N+:66]([O-:68])=[O:67])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 66737151HCID 66737151, compoundHCID 86643841HCID 86643841, compound

Product 1

HCID 66737367HCID 66737367, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a mixture of 5-(3-fluoro-benzenesulfonyl)-1-trityl-1H-indazol-3-ylamine (100 mg, 0.187 mmol), N,N-diisopropylethylamine (0.13 mL, 0.75 mmol) and dry-tetrahydrofuran (30 mL), at room temperature, was added 4-(4-methyl-piperazin-1-yl)-2-nitro-benzoyl chloride hydrochloride (66 mg, 0.206 mmol, prepared as described in Example 20). The mixture was stirred at room temperature for 1 hour then evaporated to dryness. The residue was dissolved in dichloromethane (50 mL), washed with saturated solution of sodium hydrogenocarbonate (50 mL), dried over sodium sulfate, evaporated to dryness and triturated with diethylether affording the title compound as a yellow powder (102 mg, 70% yield).

Workup

  1. dry with materialdry-tetrahydrofuran (30 mL)
  2. customthen evaporated to dryness
  3. dissolutionThe residue was dissolved in dichloromethane (50 mL)
  4. washwashed with saturated solution of sodium hydrogenocarbonate (50 mL)
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-0e2142488f8a436ebcbca4d25da2fb50
Source dataset
uspto-grants-2012_02
Patent number
US08114865B2

Reaction notes

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