Sodium Hydroxide → HCID 178434344, compound

HRID 1038837Notes

Reaction equation

HRID 1038837 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[CH2:31][CH2:30][C:24]5([O:28]C(=O)[NH:26][CH2:25]5)[CH2:23][CH2:22]4)[C:15]4[O:20][CH:19]=[CH:18][C:16]=4[N:17]=3)=[CH:8][CH:9]=2)[NH:4][N:3]=1.ClC1N=C(Cl)C2OC=CC=2N=1.O1C2(CCNCC2)CNC1=O.[OH-].[Na+]>CO>[NH2:26][CH2:25][C:24]1([OH:28])[CH2:23][CH2:22][N:21]([C:14]2[C:15]3[O:20][CH:19]=[CH:18][C:16]=3[N:17]=[C:12]([NH:11][C:7]3[CH:6]=[C:5]4[C:10]([C:2]([CH3:1])=[N:3][NH:4]4)=[CH:9][CH:8]=3)[N:13]=2)[CH2:31][CH2:30]1

Participants

6

Reactant 4

HCID 14798Sodium Hydroxide2×HCID 129541141-Oxa-3,8-diazaspiro(4.5)decan 2-oneHCID 457899682,4-Dichlorofuro[3,2-D]pyrimidineHCID 178434338HCID 178434338, compound

Product 1

HCID 178434344HCID 178434344, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

To a vial was added 8-(2-(3-methyl-1H-indazol-6-ylamino)furo[3,2-d]pyrimidin-4-yl)-1-oxa-3,8-diazaspiro[4.5]decan-2-one (0.100 g, 0.238 mmol, prepared using A from 2,4-dichlorofuro[3,2-d]pyrimidine [ArkPharm] with 1-oxa-3,8-diazaspiro[4.5]decan-2-one [Chembridge], B with Example #3, Step B and C) in MeOH (3 mL). Then aqueous NaOH (5 M, 0.715 mL, 3.58 mmol) was added. The mixture was heated in a microwave at about 100° C. for about 30 min (300 psi maximum pressure, 2 min ramp, 250 max watts). Aqueous NaOH (5 M, 0.350 mL, 1.75 mmol) was added. The mixture was heated in a microwave at about 120° C. for about 40 min (300 psi maximum pressure, 2 min ramp, 250 max watts). The mixture was filtered and the filtrate was cooled on ice and the precipitate formed was collected via filtration and dried in a vacuum oven at about 75° C. for about 15 h to give 4-(aminomethyl)-1-(2-(3-methyl-1H-indazol-6-ylamino)furo[3,2-d]pyrimidin-yl)piperidin-4-ol (0.07 g, 75%): LC/MS (Table 2, Method c) Rt=1.44 min.; MS m/z: 394 (M+H)+. Syk IC50=A

Workup

  1. customprepared
  2. temperatureThe mixture was heated in a microwave at about 120° C. for about 40 min (300 psi maximum pressure, 2 min ramp, 250 max watts)
  3. filtrationThe mixture was filtered
  4. temperaturethe filtrate was cooled on ice
  5. customthe precipitate formed
  6. filtrationwas collected via filtration
  7. customdried in a vacuum oven at about 75° C. for about 15 h

Sources & evidence

ORD record
ord-3d3e1d018e564f1d9a05b01e24cba53d
Source dataset
uspto-grants-2013_10
Patent number
US08551981B2

Reaction notes

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