Methanesulfonyl chloride → HCID 59332855, compound

HRID 1879993Notes

Reaction equation

HRID 1879993 reaction equation
[Br:1][C:2]1[CH:12]=[N:11][C:5]2[NH:6][CH2:7][CH2:8][NH:9][CH2:10][C:4]=2[CH:3]=1.[CH3:13][S:14](Cl)(=[O:16])=[O:15]>C(Cl)Cl>[Br:1][C:2]1[CH:12]=[N:11][C:5]2[NH:6][CH2:7][CH2:8][N:9]([S:14]([CH3:13])(=[O:16])=[O:15])[CH2:10][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 59332834HCID 59332834, compound

Product 1

HCID 59332855HCID 59332855, compoundYield 48.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-bromo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepine (432 mg, 1.89 mmol) and TEA (0.28 mL, 2.02 mmol) in anhydrous CH2Cl2 (20 mL) under argon was added methanesulfonyl chloride (0.16 mL, 2.06 mmol). The mixture was stirred for 12 h at room temperature. Mixture was then concentrated to a brown solid and redissolved in a 2:1 MeOH:DMSO mixture. Purification by preparative HPLC (water/acetonitrile/0.05% TFA mixture) gave the title compound (7-bromo-4-(methylsulfonyl)-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepine) (281 mg, 48%) as a yellow solid: 1H NMR (200 MHz, DMSO-d6) δ 8.02 (s, 1H), 7.68 (s, 1H), 4.39 (s, 2H), 3.48 (s, 2H), 3.39 (s, 2H), 2.79 (s, 3H).

Workup

  1. concentrationMixture was then concentrated to a brown solid
  2. dissolutionredissolved in a 2:1 MeOH
  3. customPurification by preparative HPLC (water/acetonitrile/0.05% TFA mixture)

Sources & evidence

ORD record
ord-f4b1a7c039e54cbab8b2ece1261f9b31
Source dataset
uspto-grants-2012_11
Patent number
US08318720B2

Reaction notes

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