Triethylamine → HCID 178426066, compound

HRID 1893382Notes

Reaction equation

HRID 1893382 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][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[CH:24]=[C:23]([CH3:25])[O:22][N:21]=2)[CH2:16][CH2:15]1.[CH2:28]([N:30]([CH2:33]C)CC)C.[S:35](Cl)(=[O:38])(=[O:37])N>ClCCl>[CH3:28][N:30]([CH3:33])[S:35]([N:12]1[CH2:11][C:10]2[N:6]([C:7]([C@H:14]3[CH2:15][CH2:16][C@H:17]([C:20]4[CH:24]=[C:23]([CH3:25])[O:22][N:21]=4)[CH2:18][CH2:19]3)=[N:8][N:9]=2)[C:5]2[CH:26]=[CH:27][C:2]([Cl:1])=[CH:3][C:4]=2[CH2:13]1)(=[O:38])=[O:37]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24499Chlorosulfamic acidHCID 178426061HCID 178426061, compound

Product 1

HCID 178426066HCID 178426066, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of trans-8-chloro-1-[4-(5-methyl-isoxazol-3-yl)-cyclohexyl]-5,6-dihydro-4H-2,3,5,10b-tetraaza-benzo[e]azulene (50 mg, 0.13 mmol) and triethylamine (0.036 ml, 0.26 mmol) in dichloromethane (1.3 ml) was added sulfamoyl chloride (0.028 ml, 0.26 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 (42 mg, 66%) as white solid. MS m/e: 491 ([M+H]+).

Workup

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

Sources & evidence

ORD record
ord-570d4c26e69147efb4e7cf98f03f9b74
Source dataset
uspto-grants-2013_08
Patent number
US08513238B2

Reaction notes

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