Hydrochloric Acid → HCID 66823589, compound

HRID 1910078Notes

Reaction equation

HRID 1910078 reaction equation
CC(OC([N:8](C(OC(C)(C)C)=O)[C:9]1[C:14]2[C:15]([C:18]3[CH:19]=[C:20]4[C:24](=[CH:25][CH:26]=3)[N:23](C(OC(C)(C)C)=O)[CH2:22][CH2:21]4)=[CH:16][O:17][C:13]=2[C:12]([Cl:34])=[CH:11][N:10]=1)=O)(C)C.ClC1C2OC=C(C3C=C4C(=CC=3)N(C(OC(C)(C)C)=O)CC4)C=2C(NC(OC(C)(C)C)=O)=NC=1.Cl>C(Cl)Cl>[Cl:34][C:12]1[C:13]2[O:17][CH:16]=[C:15]([C:18]3[CH:19]=[C:20]4[C:24](=[CH:25][CH:26]=3)[NH:23][CH2:22][CH2:21]4)[C:14]=2[C:9]([NH2:8])=[N:10][CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 66823388HCID 66823388, compoundHCID 66823642HCID 66823642, compound

Product 1

HCID 66823589HCID 66823589, compoundYield 164.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The products 1,1-dimethylethyl 5-[4-(bis{[(1,1-dimethylethyl)oxy]carbonyl}amino)-7-chlorofuro[3,2-c]pyridin-3-yl]-2,3-dihydro-1H-indole-1-carboxylate (81 mg, 0.138 mmol), and 1,1-dimethylethyl 5-[7-chloro-4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)furo[3,2-c]pyridin-3-yl]-2,3-dihydro-1H-indole-1-carboxylate (33 mg, 0.068 mmol) (0.206 mmol total) were combined in DCM and concentrated to a pale yellow oil. To this oil was added 1,4-Dioxane (0.5 mL) and to the resulting solution was added HCl (4 M, dioxane) (2 mL, 8.00 mmol), and the reaction stirred overnight at room temperature. The reaction mixture was concentrated to afford crude 7-chloro-3-(2,3-dihydro-1H-indol-5-yl)furo[3,2-c]pyridin-4-amine (81.5 mg, 0.227 mmol, 164% yield) as a beige solid. LC-MS (ES) m/z=286 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.64 (t, J=7.83 Hz, 2H), 3.09-3.19 (m, 2H), 6.83 (s, 2H), 6.90 (s, 1H), 7.32 (s, 1H), 7.46 (s, 1H). Note, NHs are not observed.

Workup

  1. concentrationconcentrated to a pale yellow oil
  2. additionTo this oil was added 1,4-Dioxane (0.5 mL)
  3. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-4fb18ed15b8b40b085370a9c04be65a4
Source dataset
uspto-grants-2013_12
Patent number
US08598156B2

Reaction notes

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