1,1,3,3-Tetramethylguanidine → HCID 44544423, compound

HRID 2387338Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([C:8]([CH3:37])([CH3:36])[CH2:9][C@:10]([OH:35])([C:31]([F:34])([F:33])[F:32])[CH2:11][C:12]#[C:13][C:14]2[C:19]([NH:20]C(=O)C(F)(F)F)=[CH:18][CH:17]=[C:16]([S:27]([CH3:30])(=[O:29])=[O:28])[N:15]=2)[CH:5]=[CH:6][CH:7]=1.CN(C)C(=N)N(C)C>CS(C)=O.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([CH3:37])([CH3:36])[CH2:9][C@:10]([CH2:11][C:12]2[NH:20][C:19]3[C:14](=[N:15][C:16]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:17][CH:18]=3)[CH:13]=2)([OH:35])[C:31]([F:34])([F:33])[F:32])[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 70 °C

Procedure

N-{2-[(S)-6-(3-Bromophenyl)-4-hydroxy-6-methyl-4-trifluoromethylhept-1-ynyl]-6-methanesulfonylpyridin-3-yl}-2,2,2-trifluoroacetamide (351 mg, 0.57 mmol) was dissolved in 3.4 mL of DMSO and tetramethylguanidine (0.43 mL, 3.42 mmol) was added. The mixture was stirred at 70° C. for 7 hours. Then it was diluted with ethyl acetate, washed with saturated aqueous ammonium chloride solution, and brine, dried over sodium sulfate, and concentrated in vacuo. The mixture was purified by flash chromatography (gradient 0→8% MeOH in DCM). The product was further purified by crystallization (DCM) to give (R)-4-(3-bromophenyl)-1,1,1-trifluoro-2-(5-methanesulfonyl-1H-pyrrolo[3,2-b]pyridin-2-ylmethyl)-4-methylpentan-2-ol as a white solid (181 mg, 61%).

Workup

washwashed with saturated aqueous ammonium chloride solution, and brine
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
customThe mixture was purified by flash chromatography (gradient 0→8% MeOH in DCM)
customThe product was further purified by crystallization (DCM)

Sources & evidence

ORD record: ord-67a6813c19ac41c7ac1bba06989872bf
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08268859B2

Reaction notes

Loading…