Dichloromethane → HCID 16753772, compound

HRID 1992442Notes

Reaction equation

HRID 1992442 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.C(Cl)Cl.[F:15][C:16]1[C:17]([C:32]2[N:33]=[C:34]([S:42][CH3:43])[N:35]3[CH:40]=[CH:39][N:38]=[C:37]([NH2:41])[C:36]=23)=[CH:18][CH:19]=[C:20]2[C:25]=1[N:24]=[C:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH:22]=[CH:21]2>>[F:15][C:16]1[C:17]([C:32]2[N:33]=[C:34]([S:42]([CH3:43])=[O:9])[N:35]3[CH:40]=[CH:39][N:38]=[C:37]([NH2:41])[C:36]=23)=[CH:18][CH:19]=[C:20]2[C:25]=1[N:24]=[C:23]([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[CH:22]=[CH:21]2

Participants

4

Reactant 3

HCID 6344Dichloromethane2×HCID 70297m-Chloroperbenzoic acid2×HCID 16755134HCID 16755134, compound

Product 1

HCID 16753772HCID 16753772, compound

Procedure

A solution of m-chloroperbenzoic acid (0.013 g, 0.000075 mol) in DCM (0.4 g, 0.005 mol) was added slowly to a solution of 1-(8-fluoro-2-phenyl-quinolin-7-yl)-3-methylsulfanyl-imidazo[1,5-a]pyrazin-8-ylamine (30 mg, 0.000075 mol) in DCM (2 mL, 0.04 mol) at −78° C. The reaction mixture was allowed to stir at that temp for 30 min. The reaction mixture was transferred to an ice-bath and stirred for 1 h. 50% consumption of SM was observed. The reaction mixture was stirred in ice-bath for 1 h. An additional 0.5 eq of m-chloroperbenzoic acid was added to the reaction mixture and the reaction mixture was warmed to rt and stirred for 2 h. The reaction mixture was concentrated in vacuo. Purification by prep TLC (7% MeOH in DCM) afforded the title compound as a light yellow solid. 1H NMR (400 MHz, CDCl3): δ=5.13 (br. s., 2H), 7.32 (d, J=5.05 Hz, 1H), 7.48-7.60 (m, 3H), 7.69 (dd, J=8.46, 6.44 Hz, 1H), 7.76-7.81 (m, 1H), 8.06 (d, J=8.84 Hz, 1H), 8.15 (d, J=5.05 Hz, 1H), 8.25 (dd, J=8.21, 1.39 Hz, 2H), 8.32 (dd, J=8.72, 1.39 Hz, 1H). MS (ES+): m/z 417.95 (100)[MH+]. HPLC: tR=2.63 min (Open Lynx polar—5 min).

Workup

  1. customThe reaction mixture was transferred to an ice-bath
  2. stirringstirred for 1 h
  3. custom50% consumption of SM
  4. stirringThe reaction mixture was stirred in ice-bath for 1 h
  5. stirringstirred for 2 h
  6. concentrationThe reaction mixture was concentrated in vacuo
  7. customPurification by prep TLC (7% MeOH in DCM)

Sources & evidence

ORD record
ord-8ca1138e4d70431e8386bba0a5615f21
Source dataset
uspto-grants-2010_01
Patent number
US07648987B2

Reaction notes

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