Triethylamine → HCID 178486164, compound

HRID 452550Notes

Reaction equation

HRID 452550 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]2[N:6]3[C:10]([CH2:11][NH:12][CH2:13][C:4]=2[CH:3]=1)=[N:9][N:8]=[C:7]3[C@H:14]1[CH2:19][CH2:18][C@H:17]([C:20]2[C:25]([F:26])=[CH:24][CH:23]=[CH:22][N:21]=2)[CH2:16][CH2:15]1.C(N(CC)CC)C.[CH3:36][N:37]([CH3:42])[S:38](Cl)(=[O:40])=[O:39]>ClCCl>[CH3:36][N:37]([CH3:42])[S:38]([N:12]1[CH2:11][C:10]2[N:6]([C:7]([C@H:14]3[CH2:19][CH2:18][C@H:17]([C:20]4[C:25]([F:26])=[CH:24][CH:23]=[CH:22][N:21]=4)[CH2:16][CH2:15]3)=[N:8][N:9]=2)[C:5]2[CH:27]=[CH:28][C:2]([Cl:1])=[CH:3][C:4]=2[CH2:13]1)(=[O:40])=[O:39]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 83372Dimethylsulphamoyl chlorideHCID 178505857HCID 178505857, compound

Product 1

HCID 178486164HCID 178486164, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of trans-8-chloro-1-[4-(3-fluoro-pyridin-2-yl)-cyclohexyl]-5,6-dihydro-4H-2,3,5,10b-tetraaza-benzo[e]azulene (50.0 mg, 0.126 mmol) and triethylamine (0.035 ml, 0.251 mmol) in dichloromethane (0.6 ml) was added dimethyl sulfamoyl chloride (0.27 ml, 0.251 mmol) at room temperature. Stirring for 20 h was followed by quenching with methanol (0.5 ml). The mixture was concentrated in vacuo. Preparative RP-HPLC with water (0.05% formic acid)/methanol as eluent gave the title compound (39 mg, 61%) as white solid. MS m/e: 505 ([M+H]+)

Workup

  1. customby quenching with methanol (0.5 ml)
  2. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-d27217431dd944d7a2c753dc77f6e17f
Source dataset
uspto-grants-2013_07
Patent number
US08492376B2

Reaction notes

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