Dichloromethane → HCID 86631114, compound

HRID 912660Notes

Reaction equation

[NH2:1][C:2]([C:4]1[NH:8][CH:7]=N[C:5]=1[NH:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([F:20])[CH:18]=2)[N:13]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH:12]=1)=[O:3].C(N=[C:37]=[S:38])(=O)C1C=CC=CC=1.[CH2:39](Cl)Cl>>[F:20][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[N:13]([C:21]([O:23][C:24]([CH3:25])([CH3:27])[CH3:26])=[O:22])[CH:12]=[C:11]2[CH2:10][N:9]1[C:5]2[CH:39]=[CH:7][NH:8][C:4]=2[C:2](=[O:3])[NH:1][C:37]1=[S:38]

Participants

Reactant 3

HCID 6344Dichloromethane

HCID 68284Benzoyl isothiocyanate

HCID 86631113HCID 86631113, compound

Product 1

HCID 86631114HCID 86631114, compound

Procedure

tert-Butyl 3-({[5-(aminocarbonyl)-1H-imidazol-4-yl]amino}methyl)-5-fluoro-1H-indole-1-carboxylate (0.15 g, 0.32 mmol, obtained from Example 6(b)) was dissolved in CH2Cl2. Benzoylisothiocyanate (0.06 g, 0.35 mmol) was added and the mixture was stirred at r.t. for 7 h. The mixture was concentrated in vacuo. Ammonia (7 N in methanol, 3 mL) was added and the mixture was heated at 80° C. for 1 h. The mixture was concentrated and the residue was dissolved in ethyl acetate and washed with water. The organic layer were dried (MgSO4) and concentrated in vacuo. The crude product-mixture was used in the next step without further purification. MS (ESI) m/z 414 (M−1).

Workup

concentrationThe mixture was concentrated in vacuo
additionAmmonia (7 N in methanol, 3 mL) was added
temperaturethe mixture was heated at 80° C. for 1 h
concentrationThe mixture was concentrated
dissolutionthe residue was dissolved in ethyl acetate
washwashed with water
dry with materialThe organic layer were dried (MgSO4)
concentrationconcentrated in vacuo
customThe crude product-mixture was used in the next step without further purification

Sources & evidence

ORD record: ord-630c9029d7414e88a70c84a4931d955a
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08026244B2

Reaction notes

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