HCID 59605259, compound → HCID 59606192, compound

HRID 1923181Notes

Reaction equation

HRID 1923181 reaction equation
[F:1][C:2]1[C:3]([N+:36]([O-])=O)=[C:4]([NH:8][C:9]2[N:17]=[C:16]3[C:12]([N:13]=[C:14]([CH2:19][N:20]4[CH2:25][CH2:24][CH:23]([C:26]([OH:29])([CH3:28])[CH3:27])[CH2:22][CH2:21]4)[N:15]3[CH3:18])=[C:11]([N:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)[N:10]=2)[CH:5]=[CH:6][CH:7]=1>[Pd]>[NH2:36][C:3]1[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=1[NH:8][C:9]1[N:17]=[C:16]2[C:12]([N:13]=[C:14]([CH2:19][N:20]3[CH2:21][CH2:22][CH:23]([C:26]([OH:29])([CH3:28])[CH3:27])[CH2:24][CH2:25]3)[N:15]2[CH3:18])=[C:11]([N:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)[N:10]=1

Participants

3

Reactant 1

HCID 59605259HCID 59605259, compound

Product 1

HCID 59606192HCID 59606192, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a mixture of 2-{1-[2-(3-fluoro-2-nitrophenylamino)-9-methyl-6-morpholin-4-yl-9H-purin-8-ylmethyl]piperidin-4-yl}propan-2-ol (95 mg, 0.18 mmol) in IMS (5 mL) was added 10% Pd on charcoal (20 mg) under an argon atmosphere. The vessel was evacuated and backfilled with hydrogen (the process was repeated three times). The reaction mixture was stirred at room temperature for 18 hours then filtered through celite. The filtrate was concentrated under reduced pressure and the residue was subjected to flash chromatography (Si—PCC, 0-10% MeOH in EtOAc) to give 2-{1-[2-(2-Amino-3-fluoro-phenylamino)-9-methyl-6-morpholin-4-yl-9H-purin-8-ylmethyl]piperidin-4-yl}propan-2-ol as a red oil (65 mg, 72%). LCMS (Method H): RT=0.28 min and 2.82 min, [M+H]− 499

Workup

  1. customThe vessel was evacuated
  2. filtrationthen filtered through celite
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4183813fb9c847fdb2a1f8ca134e8e85
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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