Water → HCID 178480010, compound

HRID 1498849Notes

Reaction equation

HRID 1498849 reaction equation
[CH3:1][C:2]([S@@:5]([NH2:7])=[O:6])([CH3:4])[CH3:3].[F:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:17]2[CH:18]=[N:19][C:20]([N:23]3[CH2:28][CH2:27][N:26]([C:29]4[C:34]5=[CH:35][C:36]([C:38]6[CH:39]=[N:40][N:41]([CH3:43])[CH:42]=6)=[CH:37][N:33]5[N:32]=[CH:31][N:30]=4)[CH2:25][CH2:24]3)=[N:21][CH:22]=2)=O)=[CH:11][CH:10]=1.O>C1COCC1>[F:8][C:9]1[CH:10]=[CH:11][C:12](/[C:15](/[C:17]2[CH:18]=[N:19][C:20]([N:23]3[CH2:28][CH2:27][N:26]([C:29]4[C:34]5=[CH:35][C:36]([C:38]6[CH:39]=[N:40][N:41]([CH3:43])[CH:42]=6)=[CH:37][N:33]5[N:32]=[CH:31][N:30]=4)[CH2:25][CH2:24]3)=[N:21][CH:22]=2)=[N:7]/[S@:5]([C:2]([CH3:4])([CH3:3])[CH3:1])=[O:6])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11355477tert-Butylsulfinamide, (S)-(-)-HCID 118022251HCID 118022251, compound

Product 1

HCID 178480010HCID 178480010, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(S)-2-Methylpropane-2-sulfinamide (110 mg, 0.908 mmol), (4-fluorophenyl)(2-(4-(6-(1-methyl-1H-pyrazol-4-yl)pyrrolo[2,1-f][1,2,4]triazin-4-yl)piperazin-1-yl)pyrimidin-5-yl)methanone (158 mg, 0.327 mmol) and ethyl orthotitanate (0.15 mL, 0.715 mmol) were stirred in THF (3.2 mL) at 70° C. for 18 hours. Room temperature was attained, water was added, and the products extracted into EtOAc (×2). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo while loading onto Celite. Purification of the residue by MPLC (0-10% MeOH-EtOAc) gave (S,Z)—N-((4-fluorophenyl)(2-(4-(6-(1-methyl-1H-pyrazol-4-yl)pyrrolo[2,1-f][1,2,4]triazin-4-yl)piperazin-1-yl)pyrimidin-5-yl)methylene)-2-methylpropane-2-sulfinamide (192 mg, 0.327 mmol, 100% yield) as an orange solid. MS (ES+) C29H31FN10OS requires: 586. found: 587 [M+H]+.

Workup

  1. customRoom temperature
  2. extractionthe products extracted into EtOAc (×2)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification of the residue by MPLC (0-10% MeOH-EtOAc)

Sources & evidence

ORD record
ord-62c05b8161114057b7d828889a92c77b
Source dataset
uspto-grants-2015_12
Patent number
US09200002B2

Reaction notes

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