Sodium Hydroxide → HCID 178434343, compound

HRID 1038856Notes

Reaction equation

HRID 1038856 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@H:24]5[CH2:25][NH:26]C(=O)[O:28][C@@H: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.NC[C@@H]1CCN(CC2C=CC=CC=2)C[C@H]1O.ClC1N=C(Cl)C2OC=CC=2N=1.[OH-].[Na+]>CO>[NH2:26][CH2:25][C@@H:24]1[CH2:30][CH2:31][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)[CH2:22][C@H:23]1[OH:28]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 457899682,4-Dichlorofuro[3,2-D]pyrimidineHCID 57986572rel-(3R,4R)-4-(Aminomethyl)-1-(phenylmethyl)-3-piperidinolHCID 67129967HCID 67129967, compound

Product 1

HCID 178434343HCID 178434343, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a vial was added tert-butyl 3-methyl-6-(4-((4aS,8aS)-2-oxotetrahydro-2H-pyrido[4,3-e][1,3]oxazin-7(3H,8H,8aH)-yl)furo[3,2-d]pyrimidin-2-ylamino)-1H-indazole-1-carboxylate (0.367 g, 0.706 mmol, prepared using AL from (3S,4S)-4-(aminomethyl)-1-benzylpiperidin-3-ol [Sunshine Labs], G, A with 2,4-dichlorofuro[3,2-d]pyrimidine [ArkPharm] and B with Example#3, Step B) in MeOH (5 mL). An aqueous solution of NaOH (5 M, 2.83 mL, 14.1 mmol) was added. The mixture was heated at about 80° C. for about 3 h. The resulting suspension was filtered. The precipitate obtained was discarded. Precipitation was observed in the filtrate, the precipitate was collected by filtration and dried to give (3S,4S)-4-(aminomethyl)-1-(2-(3-methyl-1H-indazol-6-ylamino)furo[3,2-d]pyrimidin-4-yl)piperidin-3-ol (0.14 g, 50%): LC/MS (Table 2, Method n) Rt=1.16 min.; MS m/z: 394 (M+H)+. Syk IC50=A

Workup

  1. customprepared
  2. filtrationThe resulting suspension was filtered
  3. customThe precipitate obtained
  4. customPrecipitation
  5. filtrationthe precipitate was collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-bb4899a070a94235912b66a8002fd265
Source dataset
uspto-grants-2013_10
Patent number
US08551981B2

Reaction notes

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