Methanesulfonyl chloride → HCID 86692006, compound

HRID 1505735Notes

Reaction equation

HRID 1505735 reaction equation
[CH2:1]([C:9]1[C:10]([C:22]([F:25])([F:24])[F:23])=[C:11]2[C:15]3=[C:16]([CH2:18][NH:19][CH2:20][CH2:21][N:14]3[CH:13]=[CH:12]2)[CH:17]=1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:26][S:27](Cl)(=[O:29])=[O:28].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH3:26][S:27]([CH:20]1[NH:19][CH2:18][C:16]2=[C:15]3[C:11](=[C:10]([C:22]([F:25])([F:24])[F:23])[C:9]([CH2:1][CH2:2][C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=4)=[CH:17]2)[CH:12]=[CH:13][N:14]3[CH2:21]1)(=[O:29])=[O:28]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 866919886-Phenethyl-7-(trifluoromethyl)-1,2,3,4-tetrahydro-[1,4]diazepino[6,7,1-hi]indole

Product 1

HCID 86692006HCID 86692006, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6-phenethyl-7-(trifluoromethyl)-1,2,3,4-tetrahydro-[1,4]diazepino[6,7,1-hi]indole (prepared as described in Example 2 above, 53 mg, 0.14 mmol), methanesulfonyl chloride (16 mg, 0.14 mmol) and diisopropylethylamine (0.072 mL, 0.42 mmol) in CH2Cl2 (3 mL) was stirred overnight. The solvent was evaporated under reduced pressure and the resulting residue purified by trituration from methanol-diethyl ether to 2-(methylsulfonyl)-6-phenethyl-7-(trifluoromethyl)-1,2,3,4-tetrahydro-[1,4]diazepino[6,7,1-hi]indole (43 mg).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe resulting residue purified by trituration from methanol-diethyl ether to 2-(methylsulfonyl)-6-phenethyl-7-(trifluoromethyl)-1,2,3,4-tetrahydro-[1,4]diazepino[6,7,1-hi]indole (43 mg)

Sources & evidence

ORD record
ord-cedb314172924fa4ac551837bff69e22
Source dataset
uspto-grants-2015_12
Patent number
US09216998B2

Reaction notes

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