1,2-Dichloroethane → HCID 86626533, compound

HRID 905923Notes

Reaction equation

HRID 905923 reaction equation
Cl.[OH:2][C:3]1[C:4]2[CH:18]=[CH:17][CH:16]=[CH:15][C:5]=2[C:6]2[C@H:7]([CH2:13][Cl:14])[CH2:8][N:9](N)[C:10]=2[CH:11]=1.[CH3:19][S:20][S:21][CH2:22][CH2:23][C:24]([NH:26][C:27]1[CH:28]=[C:29]2[C:33](=[CH:34][CH:35]=1)[NH:32][C:31]([C:36](O)=[O:37])=[CH:30]2)=[O:25].C(Cl)CCl>CC(N(C)C)=O>[Cl:14][CH2:13][C@H:7]1[C:6]2[C:5]3[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=3[C:3]([OH:2])=[CH:11][C:10]=2[N:9]([C:36]([C:31]2[NH:32][C:33]3[C:29]([CH:30]=2)=[CH:28][C:27]([NH:26][C:24](=[O:25])[CH2:23][CH2:22][S:21][S:20][CH3:19])=[CH:35][CH:34]=3)=[O:37])[CH2:8]1

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 86626534HCID 86626534, compoundHCID 131729148HCID 131729148, compound

Product 1

HCID 86626533HCID 86626533, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 5-hydroxy-3-amino-1-[S]-(chloromethyl)-1,2-dihydro-3H-benz(e)indole, hydrochloride salt (155 mg, 0.57 mmol) and 5-(3-(methyl-disulfanyl)propanamido)-1H-indole-2-carboxylic acid (170 mg, 0.55 mmol) in 7.0 ml of DMA was added EDC (300 mg, 1.56 mmol) under Ar. After stirred over night, the mixture was evaporated to dryness, purified by SiO2 chromatography (20% to 40% THF in toluene) and crystallized with THF/Toluene/Hexane to afford 218 mg (76%) of DC101SMe. 1H NMR (DMF-d7) 11.63 (s, 1H), 10.56 (s, 1H), 9.95 (s, 1H), 8.23 (s, 2H), 7.93 (d, 1H, J=8.3 Hz), 7.56 (dd, 1H, J=2.0, 8.1 Hz), 7.52 (s, 1H), 7.47 (dd, 1H, J=1.9, 8.9 Hz), 7.41 (d, 1H, J=1.7 Hz), 7.25 (d, 1H, J=1.7 Hz), 4.88 (dd, 1H, J=8.7, 11.0 Hz), 4.73 (dd, 1H, J=2.3, 10.9 Hz), 4.31 (m, 1H), 4.12 (dd, 1H, J=3.1, 11.0 Hz), 3.95 (dd, 1H, J=8.4, 11.2 Hz), 3.21 (t, 2H, J=7.1 Hz), 2.71 (t, 2H, J=7.1 Hz), 2.45 (s, 3H); 13C NMR 169.54, 161.06, 155.36, 134.21, 133.39, 132.54, 131.05, 128.39, 127.99, 123.98, 123.74, 123.46, 123.31, 118.88, 115.99, 112.87, 112.31, 106.40, 101.33, 55.93, 48.10, 42.61, 36.92, 30.81, 25.34. MS m/z+548.2 (M+Na), 550.2 (M+2+Na).

Workup

  1. customthe mixture was evaporated to dryness
  2. custompurified by SiO2 chromatography (20% to 40% THF in toluene)
  3. customcrystallized with THF/Toluene/Hexane
  4. customto afford 218 mg (76%) of DC101SMe

Sources & evidence

ORD record
ord-ddb64701aff244c8b24e76d9a538806b
Source dataset
uspto-grants-2011_09
Patent number
US08012978B2

Reaction notes

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