1,1'-Carbonyldiimidazole → HCID 16734903, compound

HRID 905924Notes

Reaction equation

HRID 905924 reaction equation
[Cl:1][CH2:2][C@H:3]1[C:11]2[C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[C:8]([OH:16])=[CH:7][C:6]=2[N:5]([C:17]([C:19]2[NH:20][C:21]3[C:26]([CH:27]=2)=[CH:25][C:24]([NH:28][C:29](=[O:35])[CH2:30][CH2:31][S:32][S:33][CH3:34])=[CH:23][CH:22]=3)=[O:18])[CH2:4]1.CCN(C(C)C)C(C)C.[C:45]([N:52]1[CH:56]=[CH:55]N=C1)(N1C=CN=C1)=[O:46].C(N(C(C)C)CC)(C)C.N[C:67]1[CH:68]=[C:69]([S:73]([OH:76])(=[O:75])=[O:74])C=C[CH:72]=1>CC(N(C)C)=O>[Cl:1][CH2:2][C@H:3]1[C:11]2[C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[C:8]([O:16][C:45]([NH:52][C:56]3[CH:55]=[C:69]([S:73]([OH:76])(=[O:75])=[O:74])[CH:68]=[CH:67][CH:72]=3)=[O:46])=[CH:7][C:6]=2[N:5]([C:17]([C:19]2[NH:20][C:21]3[C:26]([CH:27]=2)=[CH:25][C:24]([NH:28][C:29](=[O:35])[CH2:30][CH2:31][S:32][S:33][CH3:34])=[CH:23][CH:22]=3)=[O:18])[CH2:4]1

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 86626533HCID 86626533, compoundHCID 86626535HCID 86626535, compound

Product 1

HCID 16734903HCID 16734903, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of DC101SMe ((S)—N-(2-(1-(chloromethyl)-5-hydroxy-2,3-dihydro-1H-benzo[e]indole-3-carbonyl)-1H-indol-5-yl)-3-(methyldisulfanyl)propanamide, 100 mg 0.19 mmol) in 10 ml of DMA was added DIPEA (35 μl, 0.20 mmol). After stirred under Ar for 3 min., 32.0 mg (0.20 mmol) of carbonyldiimidazole was added. The mixture was stirred for 2 hours and TLC showed all DC101SMe was consumed, then fresh prepared 3-aminobenzenesulfonate diisopropylethylamine salt (65 mg, 0.21 mmol) was added. The mixture was stirred under Ar for 24 h and HPLC showed the reaction completed to form DC107SMe [(S)-3-((1-(chloromethyl)-3-(5-(3-(methyldisulfanyl)propanamido)-1H-indole-2-carbonyl)-2,3-dihydro-1H-benzo[e]indol-5-yloxy)carbonylamino)benzenesulfonic acid]. The mixture was concentrated to ˜5 ml with oil pump and used directly for next step without further purification.

Workup

  1. stirringThe mixture was stirred for 2 hours
  2. customwas consumed
  3. additionwas added
  4. stirringThe mixture was stirred under Ar for 24 h

Sources & evidence

ORD record
ord-49945e3ed3454cd9b0b739bd2f7f8504
Source dataset
uspto-grants-2011_09
Patent number
US08012978B2

Reaction notes

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