Dichloromethane → HCID 57524677, compound

HRID 882074Notes

Reaction equation

HRID 882074 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[N:20]=[C:19]3[N:21]([CH3:36])[C:22]4[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[C:24](=[O:35])[C:23]=4[C:18]3=[CH:17][CH:16]=2)[C:11](=[O:37])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=[O:39].[CH2:45]([Cl:47])[Cl:46]>>[CH2:45]([Cl:47])[Cl:46].[CH3:1][OH:8].[NH4+:12].[OH-:39].[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[N:20]=[C:19]3[N:21]([CH3:36])[C:22]4[CH2:27][CH2:26][NH:25][C:24](=[O:35])[C:23]=4[C:18]3=[CH:17][CH:16]=2)[C:11](=[O:37])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 67970839HCID 67970839, compound

Product 2

HCID 21896990Dichloromethane methanol ammonium hydroxideHCID 57524677HCID 57524677, compoundYield 33%

Conditions

Temperature
0 °C

Procedure

To a stirred solution of tert-butyl 2-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-9-methyl-5-oxo-5,7,8,9-tetrahydro-6H-pyrido[3′,4′:4,5]pyrrolo[2,3-b]pyridine-6-carboxylate (crude, ca. 0.37 mmol) in CH2Cl2 (4 mL) at 0° C. was added TFA (0.4 mL). The resulting solution was stirred at 0° C. for 1 h, quenched with saturated NaHCO3 solution (10 mL), and extracted with CH2Cl2 (3×10 mL). The combined organic extractions were dried over Na2SO4 and concentrated under reduced pressure to dryness. Preparative thin layer chromatography (200:10:1 CH2Cl2/MeOH/NH4OH) provided the title compound (49 mg, 33% over 2 steps) as an off-white solid: 1H NMR (300 MHz, DMSO-d6) δ 8.28 (d, J=8.2 Hz, 1H), 7.84 (d, J=7.7 Hz, 1H), 7.49-7.34 (m, 6H), 7.25 (br t, 1H), 6.18 (dd, J=7.8, 2.7 Hz, 1H), 6.01 (d, J=2.7 Hz, 1H), 5.17 (s, 2H), 3.76 (s, 3H), 3.53 (td, J=6.9, 2.4 Hz, 2H), 3.09 (t, J=6.9 Hz, 2H); ESI MS m/z 401 [M+H]+; HPLC (Method B) 99.0% (AUC), tR=14.6 min.

Workup

  1. customquenched with saturated NaHCO3 solution (10 mL)
  2. extractionextracted with CH2Cl2 (3×10 mL)
  3. extractionThe combined organic extractions
  4. dry with materialwere dried over Na2SO4
  5. concentrationconcentrated under reduced pressure to dryness

Sources & evidence

ORD record
ord-dcee379550f4408193710c8a36e7f188
Source dataset
uspto-grants-2015_03
Patent number
US08993765B2

Reaction notes

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