Sodium Hydroxide → HCID 178434339, compound

HRID 1038835Notes

Reaction equation

HRID 1038835 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([NH:11][C:12]3[N:13]=[C:14]([N:21]4[CH2:26][CH2:25][C:24]5[N:27]=[CH:28][N:29](S(C6C=CC(C)=CC=6)(=O)=O)[C:23]=5[CH2:22]4)[C:15]4[O:20][CH:19]=[CH:18][C:16]=4[N:17]=3)=[CH:8][CH:9]=2)[N:4](C(OC(C)(C)C)=O)[N:3]=1.ClC1N=C(Cl)C2OC=CC=2N=1.[OH-].[Na+].[NH4+].[Cl-]>C(Cl)Cl.O1CCOCC1>[N:27]1[C:24]2[CH2:25][CH2:26][N:21]([C:14]3[C:15]4[O:20][CH:19]=[CH:18][C:16]=4[N:17]=[C:12]([NH:11][C:7]4[CH:6]=[C:5]5[C:10]([C:2]([CH3:1])=[N:3][NH:4]5)=[CH:9][CH:8]=4)[N:13]=3)[CH2:22][C:23]=2[NH:29][CH:28]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 457899682,4-Dichlorofuro[3,2-D]pyrimidineHCID 68757414HCID 68757414, compound

Product 1

HCID 178434339HCID 178434339, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
65 °C

Procedure

A flask was charged with tert-butyl 3-methyl-6-(4-(3-tosyl-6,7-dihydro-3H-imidazo[4,5-c]pyridin-5 (4H)-yl)furo[3,2-d]pyrimidin-2-ylamino)-1H-indazole-1-carboxylate (0.040 g, 0.062 mmol, prepared using C from Preparation #AJ.1, A with 2,4-dichlorofuro[3,2-d]pyrimidine [ArkPharm] and B with Example #3, Step B) and 1,4-dioxane (1.0 mL). To the mixture was added 2 N aqueous NaOH, (0.094 mL, 0.19 mmol) and the mixture was heated to about 65° C. for about 4.5 h. The mixture was cooled to rt and DCM (10 mL) and saturated aqueous NH4Cl (3 mL) were added. The layers were separated and a solid remained in the aqueous layer. The solid was collected by vacuum filtration and dried overnight at about 60° C. in a vacuum oven to give 4-(6,7-dihydro-3H-imidazo[4,5-c]pyridin-5 (4H)-yl)-N-(3-methyl-1H-indazol-6-yl)furo[3,2-d]pyrimidin-2-amine (0.008 g, 33%): LC/MS (Table 2, Method c) Rt=1.60 min; MS m/z: 387 (M+H)+. Syk IC50=A

Workup

  1. customprepared
  2. customfrom Preparation #AJ.1
  3. temperatureThe mixture was cooled to rt
  4. customThe layers were separated
  5. filtrationThe solid was collected by vacuum filtration
  6. customdried overnight at about 60° C. in a vacuum oven

Sources & evidence

ORD record
ord-eac0b2071a8f40ac922a8b68732a4c0c
Source dataset
uspto-grants-2013_10
Patent number
US08551981B2

Reaction notes

Loading…