Ethanol → HCID 178422173, compound

HRID 2095711Notes

Reaction equation

HRID 2095711 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([O:9][CH:10]([F:12])[F:11])[C:3]=1[C@H:13]([C:15]1[C:23]2[C:18](=[N:19][CH:20]=[C:21]([C:24]3[CH:25]=[N:26][N:27]([CH:30]4[CH2:33][C:32](=[O:34])[CH2:31]4)[C:28]=3[CH3:29])[CH:22]=2)[NH:17][CH:16]=1)[CH3:14].[BH4-].[Na+].CCO.[NH4+].[Cl-]>>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([O:9][CH:10]([F:12])[F:11])[C:3]=1[C@H:13]([C:15]1[C:23]2[C:18](=[N:19][CH:20]=[C:21]([C:24]3[CH:25]=[N:26][N:27]([C@@H:30]4[CH2:31][C@H:32]([OH:34])[CH2:33]4)[C:28]=3[CH3:29])[CH:22]=2)[NH:17][CH:16]=1)[CH3:14]

Participants

5

Reactant 4

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 546739103-[4-(3-{(1S)-1-[2-Chloro-6-(difluoromethoxy)-3-fluorophenyl]ethyl}-1H-pyrrolo[2,3-b]pyridin-5-yl)-5-methyl-1H-pyrazol-1-yl]cyclobutanone

Product 1

HCID 178422173HCID 178422173, compound

Procedure

A mixture of 3-[4-(3-{(1S)-1-[2-chloro-6-(difluoromethoxy)-3-fluorophenyl]ethyl}-1H-pyrrolo[2,3-b]pyridin-5-yl)-5-methyl-1H-pyrazol-1-yl]cyclobutanone (10.0 mg, 0.0204 mmol), sodium borohydride (3.87 mg, 0.102 mmol) and EtOH (1 mL, 20 mmol) was stirred at rt for 30 min. Sat. NH4Cl was added, and the organic solvent was removed in vacuo. The material was extracted with DCM and water. The organic layer was concentrated in vacuo, redissolved in MeOH (0.7 mL) and purified via HPLC. The fractions containing the pure product were concentrated in vacuo to afford the title compound as a white solid. 1H NMR (400 MHz, CD3OD): δ=1.84 (d, J=7.1 Hz, 3H), 2.17 (s, 3H), 2.48-2.58 (m, 2H), 2.78-2.87 (m, 2H), 4.07-4.17 (m, 1H), 4.34-4.45 (m, 1H), 5.10 (q, J=7.2 Hz, 1H), 6.42 (br. s., 1H), 7.07-7.15 (m, 1H), 7.15-7.21 (m, 1H), 7.36 (s, 1H), 7.39 (d, J=1.0 Hz, 1H), 7.50 (s, 1H), 8.14 (br. s., 1H). MS (ES+): m/z=491.15/493.15 (100/50) [MH+]. HPLC: tR=1.41 min (polar—3 min, UPLC-ACQUITY).

Workup

  1. customthe organic solvent was removed in vacuo
  2. extractionThe material was extracted with DCM and water
  3. concentrationThe organic layer was concentrated in vacuo
  4. dissolutionredissolved in MeOH (0.7 mL)
  5. custompurified via HPLC
  6. additionThe fractions containing the pure product
  7. concentrationwere concentrated in vacuo

Sources & evidence

ORD record
ord-fff1cba79b694a2bbc5c4932476b26a7
Source dataset
uspto-grants-2013_05
Patent number
US08445510B2

Reaction notes

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